Negishi E. 2002 Handbook of organopalladium chemistry for organic synthesis / 0863 942

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Казанский национальный исследовательский технологический университет

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Химия

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freelingyne

(cf.Table5)

( )-calicheamicinone

(cf.Table5)

(−)-tricholomenynA

(cf.Table5)

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[93]	[155]	[156]	[157]
NA	60	55	59
2	CuI Et	TEA CuI	2
CuI BuNH-n	CuI Et	TEA CuI	CuI BuNH-n
	N
	3

4 ) 3 Pd(PPh

Br OH

TMS
neooxazolomycin	(cf.[93])
34

		2
		)
3		3
3		Pd(PPh
4
)
Pd(PPh		Cl
		2
SPh		O
SPh	O	O
	O	BPSO
I				I
				I
O
OH	OMOM		O
OH	OMOM		O
	O OMOM		OO MEMMEM			17
	11		O		H
C)			O			8
	2				C
C(H
C(H		MEMO
H		MEMO
	3
(+)-4-deoxy-	gigantecin (cf.below)	mucocin (cf.below)
37		37

2
)
3
Pd(PPh
2
Cl
TMS
	Cl


		OH
	2
O		CH


O
γ′calicheamicin1	related (cf.[157])
52

[158]

2 CuI PrNH -n

4 ) 3 Pd(PPh

Cl Cl

TBSO

[158]

2 CuI BuNH -n

4 ) 3 Pd(PPh

TBSO O

CO 3 H

	[159]−[162]
	76
	2
	CuI BuNH-n	PPh
		3
	2
	Pd(OAc)
Cl	TMS

O	O	OTBS
N
O	TBSO
O

calicheamicin esperamicin related (cf.[158])	γ′calicheamicin1	(cf.[162])
	52

(Continued )

903

TABLE 5. (Continued )

Catalyst Additive Yield (%) Reference

R′X

RC CH

Name

n C

[163]		[163]
80		88
2		2
CuI n-BuNH		CuI n-BuNH
4		4
)		)
3		3
Pd(PPh		Pd(PPh
	Cl	O Cl MEM
	Cl
		TBSO
		TBSO
	OMEM

		CO

HO
		3
		H

calicheamicin

esperamicin

(cf.[163])

[164]

[165]

CuI

CuI Et

CuI

PrNH-n

)

Pd(PPh

TBDPS

TMS

OTf

OCH

OPiv

OTBS

TBDPS

EtO

O O

calicheamicin

esperamicin related

(cf.[164])

neocarzinostatin

chromophore

(cf.below)

[133]
70−75
CuI	NH
CuI	Et
	2
2
)
3
Pd(PPh
2
Cl
	OH
	I

C 2 TBSOH

neocarzinostatin TBSO chromophore (cf. below)

904

O	O
HO

O		mucocin
OO HH
	17
O		H
	8
		C

O	O
O
O

O	O

2 ArCO

OH O	OH	4-deoxygigantecin
O	OH	(+)-
	OH
11
C)
2
C(H
3
H

SugarO

neocarzinostatin

chromophore

905

TABLE 6. Alkyne Synthesis Involving Alkynylmetals or Alkynylhalides (cf. Sect. III.2.8.2)

Catalyst Additive Yield (%) Reference

R′X

Name

n C

75 [166]

2 Pd(PhCN) 2 Cl

TMS

Br)CHOEt 3 O(CH 2 CH 2 CHCH

ClZnHC

marasin

	[167]			[136]
	37			74
	DMF					CuI
	2			2
	)			)
	3			3
	Pd(PPh					Pd(PPh
	2			2
	Cl					Cl
					O
			O				OH



			I	I
				3
	3						SnBu
SnBu							SnBu
			O




		O
(Z)-scobinolide		(E)-scobinolide	cleviolide			( )-harveynone (cf.Table5)
10	10		10	11

65 [168]

4 ) 3 Pd(PPh

MgBr

TMS

5-(3-buten-1-ynyl)- 2,2′-bithienyl

5-(3-buten-1-ynyl) 2,2-bithienyl

cleviolide

scobinolide

(E)-

scobinolide

(Z)-

marasin

906

[120]	[120]	[129]
94	82	72
		DMF
4	4	4
)	)	)
3	3	3
Pd(PPh	Pd(PPh	Pd(PPh
	3
	CH	I
	2
OTHP	NHCO			O
	O				O


	O
	O
I	O				I


			TBSO
I	ZnBr		TBSO
MgBr	ZnBr		SnMe
		3

[169]
98
CuI	N
CuI	Et
	3
2
)
3
Pd(PPh
2
Cl

OH	O	OTBS
	I
		3
		SnBu

80 [170]

	2
	)
	3
	Pd(PPh
	2
	Cl
OTBDPS		COCl
O		CO
O

	3
		H
	3
	SnBu



	TMS

18 PsiA (cf. below)

[54]	(Continued)
72

	4
	)
	3
	Pd(PPh
	onestep
	Br
Br	I
ZnBr	ZnBr

xerulin	(cf.Table5)
18

907

TABLE 6. (Continued )

Catalyst Additive Yield (%) Reference

R′X

Name

n C

[54]	[54]	[54]	[171]	[171]
65	70	77	61−71	61−71

)

Pd(PPh

TBS

OTBS

OTBDPS

ZnBr

SnBu

TBS

LTB4

xerulin

(cf.Table

3-(R)-OH-

4 ) 3 Pd(PPh

OTBS

		Br
	3
H			SnBu
			O

TBDPSO
TBDPSO			H
			CO
	3
	3-(S)-OH-LTB4

58 [62]

Pd(PPh		OH R				R(-3H=)-OH-LTB4 S(-3OH)-OH-LTB4
			R ′
4
)
3
						OH,R′ H,R′=

			OH
						R= R=
Br
	Br


					17
					H
ZnCl					8
					C
					OH
					OH
		O		O		PsiA
(2E,6E,8E)-N-(2-methyl- propyl)-2,6,8-hexadeca trien-10-ynamide


		(cf.Table3)
20

908

87 [172]

2 CN) 3 Pd(CH 2 Cl

I N

3 SnBu

21 terbinafine

[173]	[130]−[132]
68	80

)

Pd(PPh

OAc

OTBS

CMgBr

SnMe

epiantillatoxin

( )-dynemicinA

(cf.Table5)

(Continued )


O		N			N	O	epiantillatoxin
	O			O

				H
			MeN		O

N		terbinafine

909

TABLE 6. (Continued )

Catalyst Additive Yield (%) Reference

R′X

Name

n C

[133]	[125]	[126]	[127]	[128]	[134]
70−80	32	62	60	72	75

4 ) 3 Pd(PPh

	OH
I		3
I	I	SnBu
SnBu



C
2
TBSOH
neocarzinostatin	chromophore	(cf.Table5)

4	4	4
)	)	)
3	3	3
Pd(PPh	Pd(PPh	Pd(PPh

		SnBu		3
		SnBu		OTBS SnBu
		3
Br	TES		Br		Br
O		OTES
					HO
	HO		HO	TBSO	HO
neocarzinostatin	chromophore (cf.Table5)		neocarzinostatin related (cf.Table5)

OTES

4 ) 3 Pd(PPh

3 SnBu

		4
		)
		3
		Pd(PPh
			OBn
		Br
	OTES		TBSO
		3
		3
		SnBu
HO		SnBu
			TBSO

910

TABLE 7. Allylation, Benzylation, and Propargylation (cf. Sect. III.2.9)

Catalyst Additive Yield (%) Reference

R′X

Name

n C

51 [178]

4 ) 3 Pd(PPh

3 SnBu

2 Al(Et)

THPO

Z(33,6 Z,6- -)dien - -1 -dodecaol

[174]	[174]	[175]
86	77	32
		NaOH
4	4	4
)	)	)
3	3	3
Pd(PPh	Pd(PPh	Pd(PPh

		2
Cl	Cl		B(sia)
		2	Br
2
Al(Me)		Al(Me)

α-farnesene	(Z)-α-farnesene	humulene
15	15	15

72 [49]

2 CN) 3 Pd(CH 2 Cl

Me 2 CO

3 SnBu

juvenilececropia hormone - 16 C

11 H 5 C

humulene

(Z)- -farnesene

-farnesene

(3Z,6Z)-dodeca-3,6-dien-1-ol

(Continued )

911

TABLE 7. (Continued )

Reference		[179],[180]
Yield(%)		50−60
Additive
Catalyst		4		OTBDPS
Catalyst		Pd(PPh		OTBDPS
		)
		3
				O
				O
R′X			O


	MeOOC	Br
		3
		SnBu
RM
		THPO
Name		acerosolide
		-
		(+)
		−
n		21
C		21

[181]	[182]
74	NA

4				4
)				)
3				3
Pd(PPh				Pd(PPh
		COOMe		O	O
AcO		11	MeO	Br O	TBDPSO
			C
			2
		H
		5	OH	SnBu
		C	OH	SnBu
				3
BO				THPO


LiEt
3
deoxypro-		2	[181])(cf.	gorgiacerone
(+)	taglandinE methylester		[181])(cf.	gorgiacerone
-11-
−
21				21

[183]

NaOH

4 ) 3 Pd(PPh

Me 2 CO

TMS

B 2 ) 11 H 6

C-(c

-6 PGs-keto

[177]

MeO

)

Pd(PPh

COOMe

TBSO

MeO

AlMe

coenzyme

3 Qcoenzyme

6-keto-PGs

( )-acerosolide gorgiacerone

912

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