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Казанский национальный исследовательский технологический университет

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Химия

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Organic Reaction Mechanisms 1997

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C6H5Cl, reflux

22 h

NHAc

AcNH

Si(Me)2But

Br O

(107)

Si(Me)2But

		O



Me	N		NHAc
Me	N		NHAc

		O
	(108) 66%
SCHEME 38
M

! " M

# M

M M

" !


			OMe			OMe		OMe
MeO		MeO		OMe			MeO		OMe
		MeO

					O2*
						O


O				CHCl3, 0 °C, 15 min		O
				CHCl3, 0 °C, 15 min		O

		O
	O	O
	O	HN					HN
		HN	O
								O


		Me					Me
							Me
		(109)				85%

SCHEME 39

M! "

TBSO

C6H5Me +

Ph	N	Me	CHO 0 °C to rt
Ph		Ph

(110)

TBSO				Me
TBSO
			CHO	Me
			CHO
			Me
			Me
Ph		N	Ph		Me
					Me


				Me	Me
	(111)		94%	(–)-α-elemene
				88% ee

SCHEME 40

# #

M #

21 °C, 1.5 h

MOMO

(112)

(113)

79%

SCHEME 41

N O

hν/benzil

C6H6, rt

(114)

(115)

R = H, Me

Ar = 4-XC6H4

SCHEME 42

J M

K M

M #

# #

			#	#


		#
#
	M

TIPSO

OTIPS

Me O

TiCl4/SbPh3/Me3Al

hexanes/CH2Cl2

OTIPS

89%

TIPSO

OTIPS

(116)

(117)

OTIPS

HO HO

OTIPS

(–)-cassioside

(118)

SCHEME 43

					M
	O			O			O
				O			O
	R1				+		R1
							R1
		CH2Cl2, –20 °C		R1			R2
		CH2Cl2, –20 °C					R2
			O			O
O	R2			R2
(119)				(120)	(121)
R1 = (S)S-SOTol, H					(121)
R1 = (S)S-SOTol, H
R2 = H, (S)S-SOTol							EtOAc,
R2 = H, (S)S-SOTol							EtOAc,
							reflux, 24 h
							O
						O


			garudane
	(122)
			SCHEME 44

cyclopentadiene

(123)
			SCHEME 45
NO2	O
		OPri	O
			O


O	+
O			Ph	SiMe2Ph



O
(124)			(125)
			H	OG*
		O	O	OG*
		O	N
		PriO2C	N
		PriO2C
		H		SiMe2Ph

73%

SCHEME 46

O O

MAPh

–14 °C, C6H5Me

H HO H OH

(+)-crotanecine

(126)

! "

J M

O	+ O–	*GO
O	+ O–
	N
Me		+		MAPh (3 equiv.)
				MAPh (3 equiv.)

					CH2Cl2, –25 °C
					CH2Cl2, –25 °C
	Ph
	(127)		(128)
G* = trans-(1R,2S)-phenylcyclohexanol
		OR		OR

NiCl2/NaBH4

EtOH

H2N Me Ph

(129)

R = H, 72%

Ac2O/py

R = Ac, 77%

93% ee

SCHEME 47

–O + O OG* N

95%

NaHCO3 C6H6, reflux

O O

	N	Ph
	N	OG*
		OG*
		Me
		96%

2 equiv. ZnCl2

CH2Cl2, 25 °C

63%

5 mM in PhMe

6 equiv. BF3.Et2O

Me H

10% NaOMe/MeOH

reflux

92%

(130)

82%

SCHEME 48

CO2Et

EtO2C

Br–

DBU

CO2Et

heat

–HBr

50%

N H

CO2Et

SCHEME 49

)2 CH2

DMF or DME

(131)

(132)

R = Bz, SO2Ph, Ac

H N

CO2Et

	)	CH2
	)	2
		2

(133)

SCHEME 50

M M M

SEt

Ac2O, p-TsOH

(134)

(135)

SEt

–EtS

H+

(136)

SCHEME 51

M #


	O2N				O2N				O2N
	N	EtOCH	CH2			N	+		N
	O					O			O

				–O

O2N	N+				+	N+	–O	+	N+
	N+				N	N+		N	N+
					N			N	H O–
	O–				H	O–			H O–
	(137)
					EtO				OEt
					(138)				(139)

EtO	O + O–
	N
		N
		N
–O		O
–O		N+
N		H O–

O
O
EtO
	(140)
SCHEME 52

# J

# #

# $ $

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