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212 Chemistry and Biology of Beta-Lactams
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SCHEME 6.34 Reagents and condition: a) BuLi; b) i) CSI, Na2CO3, toluene; ii) Red-Al; c) BEMP or K2CO3, TBABr or
CsCO3; d) TBAI; e) TBABr, K2CO3.
SCHEME 6.35 Reagents and condition: a) i) TiCl4, (C8H17)3N; ii) D; b) i) (C8H17)3N; ii) D; c) Ce(NH4)2(NO3)6.
SCHEME 6.36 Reagents and condition: a) i) TiCl4, (C8H17)3N; ii) D; b) Ce(NH4)2(NO3)6.
6.2.9 Synthesis of Beta-Lactams Using Modified Polyethylene Glycol
A soluble polymer-supported approach was developed by Cozzi and others
lactams using modied poly(ethylene glycol) (PEG)
imine was reacted with titanium enolate of pyridylthiobutanoate by using an enolate/imine condensation
141
142, 143
(Scheme 6.35 and 6.36). The polymer-bound
for the synthesis of beta-
213Solid Support-Mediated Beta-Lactam Synthesis
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approach
144
and acid chloride by using a [2+2] cycloaddition reaction.
145
As a result of treating pyridylthiobutanoate with TiCl4, titanium enolate of pyridylthiobutanoate was produced, which was then
reacted with imine to produce beta-lactams that were bound to polymers. As a result of the reaction
between imine and phenoxyacetylchloride in the presence of trioctylamine, beta-lactams bound to
respective polymers were also formed. After the beta-lactams were cleaved from the resin by using CAN,
the cis-beta-lactams were obtained in good yield (Scheme 6.35).
The polymer-supported synthesis of beta-lactams was further investigated using compounds that were
enantiomerically pure (Scheme 6.36). In order to obtain trans-beta-lactams, the imine was reacted with
the titanium enolate of the compound followed by the cleavage with CAN.
6.2.10 Synthesis of Beta-Lactams Using Wang Resin
The solid-phase synthesis of beta-lactam-peptides and their opened variants has been reported (Scheme
6.37–6.39).
146
The N-Fmoc-protected tripeptide scaffolds E, F, and G were installed onto a Wang resinsupported peptide using a solid-phase synthesis technique based on Fmoc. In order to remove the FMOcprotecting group, piperidine was used in DMF, followed by the addition of two amino acids (leucine and
beta-alanine). To remove the protecting group and to separate the peptide from the resin, the resultant
peptide was then treated with an aqueous solution of TFA. Instead of the beta-lactam peptides that
were expected, opened variants were obtained in place of the expected beta-lactam peptides, taking into
account the possible mechanism for the unusual opening of the N1–C4 beta-lactam ring.
147, 148
The aque-
ous TFA treatment is shown in the following scheme (Scheme 6.37).
For the purpose of avoiding unusual beta-lactam ring opening, the Wang resin was replaced by an
amino PEGA resin bearing a base-labile hydroxymethylbenzoic acid (HMBA) linker
149
(Scheme 6.38).
TFA was used to remove the tert-butyl-protecting group, and then it was immediately acetylated using
Ac2O in pyridine. It was demonstrated that solid-supported beta-lactam peptides can be prepared as
described in Scheme 6.37 and that the peptides can be nally cleaved from the resin using 0.1 M aqueous
sodium hydroxide to yield the corresponding free beta-lactam peptides (Scheme 6.39).
6.2.11 Synthesis of Beta-Lactams by Supported Rhodium Nanoparticles
The use of supported rhodium nanoparticles to catalyze the synthesizing of alpha-methylene-beta-lactams was demonstrated (Scheme 6.40).
SCHEME 6.37 Reagents and condition: a) E, F, or G, HBTU, DIEA; b) piperidine/DMF; c) end of SPPS; d) TFA, TIS,
H2O.
150
A set of nanoparticles was prepared using the metal vapor
214 Chemistry and Biology of Beta-Lactams
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SCHEME 6.38 Description of mechanism behind the reaction.
SCHEME 6.39 Reagents and condition: a) i) Fmoc-V-OH, DIC, DMAP; ii) Fmoc-T(tBu)-OH, HBTU, DIEA; iii) TFA; iv)
Ac2O, Py; b) i) SPPS; ii) piperidine/DMF (1:4); iii) 0.1M NaOH.
SCHEME 6.40 Rhodium-catalyzed synthesis of beta-lactams.
synthesis (MVS) technique using rhodium-solvated metal atom (SMA)-derived species as the starting
material. The silylcarbocyclization of propargyl amines with a heterogeneous catalyst
151, 152
in the presence of 10 mol% DBU led to good yields of beta-lactams in these reactions. Based on the results of the
leaching experiments, it has been determined that rhodium nanoparticles are the active species and not
the heterogeneous matrix.
6.2.12 Synthesis of Beta-Lactams by Solid-State Ionic Chiral Auxiliary Method
By utilizing a solid-state ionic chiral auxiliary method, Scheffer and Wang
153
developed a method for the
synthesis of beta-lactam through the photolysis of crystals of a carboxylic acid-containing N,N-dialkyla
rylglyoxylamide
154–156
(Scheme 6.41). Through palladium-catalyzed carbonylation followed by oxidation,
215Solid Support-Mediated Beta-Lactam Synthesis
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SCHEME 6.41 Reagents and condition: a) SeO2, Py; b) (COCl)2, (i-C3H7)NH; c) LiOH, MeOH; d) i) hv, crystal; ii) CH2N2.
coupling, and hydrolysis, the appropriate compound was converted into an acid. The crystalline salts
of the acid were prepared by treating it with L-(-)prolinamide, or with (R)-(+)-1-phenylethylamine, and
then irradiating the solution with a wavelength ≥300 nm to give enantiomerically pure beta-lactam
derivatives.
6.3 Conclusion
According to the description of the results on enantioselectivity and diastereoselectivity of solid-supported synthesis, the results are similar to those obtained by solution-phase synthesis. Only a very few
examples have been reported in which the steric bulk of certain polymer-based resins has resulted in different stereostructures. It is intriguing to see the results obtained by solid-phase synthesis since the solid
components seem to have no effect on the stereochemistry of the product that has been synthesized. In
spite of this, there is also a claim made that the reaction mediated by solid support also follows a similar
mechanism that was proposed for the classical method as well. According to the results, it seems that the
steric factors and electronic contributions exerted by the solid support have no effect whatsoever on the
stereochemistry of the product.
There have been reports that the stereochemistry of some beta-lactams can be altered by microwave
irradiation at a high power and that this can occur without any isomerization taking place between the
less stable and more stable beta-lactams. It is more likely that microwave irradiation alters the structures
of the intermediate transition states in the reactions during microwave irradiation. The same type of
stereochemical results are obtained with imines that contain polycyclic rings at the nitrogen atom in
order to achieve this type of unprecedented stereochemistry. Under microwave and ultrasonic methods,
it would be highly interesting to study the solid-phase synthesis of beta-lactams under microwave and
ultrasonic conditions. There is no doubt that these challenging methods will add a lot of information to
what is currently known about beta-lactams in the coming years.
216 Chemistry and Biology of Beta-Lactams
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Acknowledgments
AD is grateful to CEA-Grenoble, Joseph Fourier University, University of Göttingen, and University of
California, Los Angeles, for their support. BKB is grateful to the US NIH, the US NCI, Texas Kleberg
Foundation, Stevens Institute of Technology, University of Texas MD Anderson Cancer Center, University
of Texas-Pan American, and Community Health Systems of Texas for their nancial and moral support
to his research. AD and BKB are also grateful to their current employer, Prince Mohammad Bin Fahd
University. The authors are grateful to Dr. Prakash Parvatkar and Dr. P. S. Parameswaran for their contribution in this eld.
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53. Das A, Banik BK. Chapter 1 – Anticancer activity of natural compounds from leaves of the plants. In:
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54. Das A, Banik BK. Chapter 2 – Anticancer activity of natural compounds from stems/barks of the
plants. In: Krishna Banik B, Das A, eds. Natural Products as Anticancer Agents. Elsevier; 2024:49–86.
doi:10.1016/B978-0-323 -9 9710-2.00010-X
55. Das A, Banik BK. Chapter 3 – Anticancer activity of natural compounds from roots of the plants.
In: Krishna Banik B, Das A, eds. Natural Products as Anticancer Agents. Elsevier; 2024:87–132.
doi:10.1016/B978-0-323-99710-2.00009-3
56. Das A, Banik BK. Chapter 4 – Anticancer activity of natural compounds from fruits and vegetables.
In: Krishna Banik B, Das A, eds. Natural Products as Anticancer Agents. Elsevier; 2024:133–178.
doi:10.1016/B978-0-323-99710-2.00001-9
57. Banik BK, Das A. Chapter 5 – Anticancer activity of natural compounds from marine animals.
In: Krishna Banik B, Das A, eds. Natural Products as Anticancer Agents. Elsevier; 2024:181–236.
doi:10.1016 / B978-0-323-99710 -2 .00012-3
58. Banik BK, Das A. Chapter 6 – Anticancer activity of natural compounds from marine plants. In: Krishna
Banik B, Das A, eds. Natural Products as Anticancer Agents. Elsevier; 2024:237–284. doi:10.1016/
B978-0-323-99710-2.00003-2
59. Das A, Banik BK. Chapter 7 – Anticancer activity of natural compounds from bacteria. In: Krishna
Banik B, Das A, eds. Natural Products as Anticancer Agents. Elsevier; 2024:287–328. doi:10.1016/
B978-0-323-99710-2.00011-1
60. Banik BK, Das A. Chapter 8 – Anticancer activity of natural compounds from fungi. In: Krishna
Banik B, Das A, eds. Natural Products as Anticancer Agents. Elsevier; 2024:329–366. doi:10.1016/
B978-0-323-99710-2.00004-4
61. Banik BK, Das A. Chapter 9 – Anticancer drugs from hormones and vitamins. In: Krishna Banik
B, Das A, eds. Natural Products as Anticancer Agents. Elsevier; 2024:369–414. doi:10.1016/
B978-0-323-99710-2.00006-8
62. Banik BK, Das A. Chapter 10 – Future prospects in anticancer natural products. In: Krishna Banik
B, Das A, eds. Natural Products as Anticancer Agents. Elsevier; 2024:415–426. doi:10.1016/
B978-0-323-99710-2.00002-0
63. Yadav RN, Hossain MdF, Das A, Srivastava AK, Banik BK. Organocatalysis: A recent development on
stereoselective synthesis of o-glycosides. Catalysis Reviews. 2022;0(0):1–118. doi:10.1080/01614940.20
22 .2041303
64. Das A, Banik BK. Versatile synthesis of organic compounds derived from ascorbic acid. Curr
Organocatal. 20 2 2;9 (1):14 –33.
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65. Das A, Banik BK. 15 – Versatile thiosugars in medicinal chemistry. In: Banik BK, ed. Green Approaches
in Medicinal Chemistr y for Sustainable Drug Design. Advances in Green and Sustainable Chemistry.
Elsevier; 2020:549–574. doi:10.1016/B978-0-12-817592-7.00015-0
66. Das A, Yadav RN, Banik BK. Ascorbic Acid-mediated Reactions in Organic Synthesis. Curr
Organocatal. 2020;7(3):212–241.
67. Das A, Banik BK. Microwaves in Chemistry Applications: Fundamentals, Methods and Future Trends.
Elsevier Science; 2021.
68. Das A, Banik BK. Chapter 1 – Foundational principles of microwave chemistry. In: Das A, Banik B,
eds. Microwaves in Chemistry Applications. Advances in Green and Sustainable Chemistry. Elsevier;
2021:3–26. doi:10.1016/B978-0-12-822895-1.00005-9
69. Das A, Banik BK. Chapter 2 – Microwave equipment for chemistry. In: Das A, Banik B, eds. Microwaves
in Chemistry Applications. Advances in Green and Sustainable Chemistry. Elsevier; 2021:27–59.
doi:10.1016/B978-0-12-822895-1.00002-3
70. Das A, Banik BK. Chapter 3 – Modeling and interpreting microwave effects. In: Das A, Banik B,
eds. Microwaves in Chemistry Applications. Advances in Green and Sustainable Chemistry. Elsevier;
2021:61–104. doi:10.1016/B978-0-12-822895-1.00007-2
71. Das A, Banik BK. Chapter 4 – Microwave-assisted synthesis of oxygen- and sulfur-containing organic
compounds. In: Das A, Banik B, eds. Microwaves in Chemistry Applications. Advances in Green and
Sustainable Chemistry. Elsevier; 2021:107–142. doi:10.1016/ B978-0-12-822895 -1.0 0 010 -2
72. Das A, Banik BK. Chapter 5 – Microwave-assisted synthesis of N-heterocycles. In: Das A, Banik B,
eds. Microwaves in Chemistry Applications. Advances in Green and Sustainable Chemistry. Elsevier;
2021:143 –198. doi:10.1016/B978-0-12-822895-1.00006-0
73. Das A, Banik BK. Chapter 6 – Microwave-assisted oxidation and reduction reactions. In: Das A, Banik
B, eds. Microwaves in Chemistry Applications. Advances in Green and Sustainable Chemistry. Elsevier;
2021:199–244. doi:10.1016/B978-0-12-822895-1.00001-1
74. Das A, Banik BK. Chapter 7 – Microwave-assisted enzymatic reactions. In: Das A, Banik B, eds.
Microwaves in Chemistry Applications. Advances in Green and Sustainable Chemistry. Elsevier;
2021:245–281. doi:10.1016/B978-0-12-822895-1.00009-6
75. Das A, Banik BK. Chapter 8 – Microwave-assisted sterilization. In: Das A, Banik B, eds. Microwaves
in Chemistry Applications. Advances in Green and Sustainable Chemistry. Elsevier; 2021:285–328.
doi:10.1016/B978-0-12- 822895 -1.0 0 011-4
76. Das A, Banik BK. Chapter 9 – Microwave-assisted CVD processes for diamond synthesis. In: Das A,
Banik B, eds. Microwaves in Chemistry Applications. Advances in Green and Sustainable Chemistry.
Elsevier; 2021:329–374. doi:10.1016/B978-0-12-822895-1.00004-7
77. Das A, Banik BK. Chapter 10 – Future trends in microwave chemistry and biology. In: Das A, Banik B,
eds. Microwaves in Chemistry Applications. Advances in Green and Sustainable Chemistry. Elsevier;
2021:375–384. doi:10.1016/B978-0-12-822895-1.00003-5
78. Das A, Banik BK. Microwave-induced biocatalytic reactions toward medicinally important compounds.
Phys Sci Rev. 2022;7(4–5):507–538. doi:10.1515/psr-2021-0064
79. Das A, Banik BK. 3 Microwave-induced biocatalytic reactions toward medicinally important com-
pounds. In: 3 Microwave-Induced Biocatalytic Reactions toward Medicinally Important Compounds.
De Gruyter; 2022:57–88. doi:10.1515/9783110732542 -003
80. Das A, Yadav R, Banik B. Microwave-induced surface-mediated highly efcient regioselective nitration
of aromatic compounds: Effects of penetration depth. Asian J Chem. 2021;33:2203–2206. doi:10.14233/
ajchem.20 21.2 3131
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