Stereoselective synthesis of macrolactin A analogues .2. The C-1-C-14 fragment

被引：20

作者：

Benvegnu, TJ ^{[1
]}

Gree, RL ^{[1
]}

机构：

[1] ECOLE NATL SUPER CHIM RENNES,CNRS URA 1467,LAB SYNTH & ACTIVAT BIOMOL,F-35700 RENNES,FRANCE

来源：

TETRAHEDRON | 1996年 / 52卷 / 36期

关键词：

D O I：

10.1016/0040-4020(96)00667-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthetic approach to the C-1-C-14 part of Macrolactin A analogues is presented. The sequence involving hydroboration-Pd degrees coupling reaction was found to be the most efficient in term of chemio- and stereo-selectivity to prepare the sensitive and functionalized E,Z diene unit. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：11821 / 11826

页数：6

共 10 条

[1] BENVEGNU T, 1994, SYNLETT, P505
[2] BENVEGNU T, 1990, THESIS U RENNES 1 FR
[3] A STEREOSPECIFIC SYNTHESIS OF CONJUGATED (E,Z)-ALKADIENES AND (E,E)-ALKADIENES BY THE PALLADIUM-CATALYZED REACTION OF (E)-1-ALKENYLBORONIC ACIDS AND 1-ALKENYL IODIDES
CASSANI, G
MASSARDO, P
PICCARDI, P
[J]. TETRAHEDRON LETTERS, 1983, 24 (24) : 2513 - 2516
[4] A PRACTICAL AND GENERAL ENANTIOSELECTIVE SYNTHESIS OF CHIRAL PROPA-1,2-DIENYL AND PROPARGYL CARBINOLS
COREY, EJ
YU, CM
LEE, DH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (02) : 878 - 879
[5] SUZUKI-TYPE CROSS-COUPLING REACTIONS USING PALLADIUM-WATER SOLUBLE CATALYST - SYNTHESIS OF FUNCTIONALIZED DIENES
GENET, JP
LINQUIST, A
BLART, E
MOURIES, V
SAVIGNAC, M
VAULTIER, M
[J]. TETRAHEDRON LETTERS, 1995, 36 (09) : 1443 - 1446
[6] ASYMMETRIC-SYNTHESIS OF HOMOPROPARGYLIC ALCOHOLS FROM ALDEHYDES AND ALLENYLTRI-N-BUTYLSTANNANE
KECK, GE
KRISHNAMURTHY, D
CHEN, X
[J]. TETRAHEDRON LETTERS, 1994, 35 (45) : 8323 - 8324
[7] A HIGHLY EFFICIENT SYNTHESIS OF (Z) GAMMA-IODO ALLYLIC ALCOHOLS
MAREK, I
ALEXAKIS, A
NORMANT, JF
[J]. TETRAHEDRON LETTERS, 1991, 32 (39) : 5329 - 5332
[8] NOVEL AND CONVENIENT METHOD FOR THE STEROSPECIFIC AND REGIOSPECIFIC SYNTHESIS OF CONJUGATED ALKADIENES AND ALKENYNES VIA THE PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF 1-ALKENYLBORANES WITH BROMOALKENES AND BROMOALKYNES
MIYAURA, N
YAMADA, K
SUGINOME, H
SUZUKI, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (04) : 972 - 980
[9] STEREOCONTROLLED TOTAL SYNTHESIS OF (5S,6R)-(7E,9E,11Z,14Z)-5-6-DIHYDROXY-7,9,11,14-ICOSATETRAENOIC, (5S,6S)-(7E,9E,11Z,14Z)-5-6-DIHYDROXY-7,9,11,14-ICOSATETRAENOIC, (5R,6R)-(7E,9E,11Z,14Z)-5-6-DIHYDROXY-7,9,11,14-ICOSATETRAENOIC, AND (5R,6S)-(7E,9E,11Z,14Z)-5,6-DIHYDROXY-7,9,11,14-ICOSATETRAENOIC ACID (5,6-DIHETE) METHYL-ESTERS
NICOLAOU, KC
RAMPHAL, JY
PALAZON, JM
SPANEVELLO, RA
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (05): : 587 - 588
[10] DRAMATIC RATE ENHANCEMENT OF SUZUKI DIENE SYNTHESIS - ITS APPLICATION TO PALYTOXIN SYNTHESIS
UENISHI, J
BEAU, JM
ARMSTRONG, RW
KISHI, Y
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (15) : 4756 - 4758

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