Novel asymmetric syntheses of (-)-malyngolide and (+)-epi-malyngolide

被引：31

作者：

Enders, D

Knopp, M

机构：

[1] Institut für Organische Chemie, Rheinisch Westfalische TH Aachen, D-52074 Aachen

来源：

TETRAHEDRON | 1996年 / 52卷 / 16期

关键词：

D O I：

10.1016/0040-4020(96)00236-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The diastereo- and enantioselective synthesis of (-)-malyngolide [(S,R)-1], an antibiotic against Mycobacterium smegmatis and Streptococcus pyogenes, using the asymmetric Carroll rearrangement as key step is described. Furthermore, the diastereo- and enantioselective synthesis by double alpha,alpha'-alkylation using SAMP/RAMP hydrazone methodology affords the diastereomer (+)-epi-malyngolide [(S,S)-1]. (C) 1996 Elsevier Science Ltd.

引用

页码：5805 / 5818

页数：14

共 45 条

[1] STEREOSELECTIVE REACTIONS .21. ASYMMETRIC ALKYLATION OF ALPHA ALKYL BETA-KETO-ESTERS TO ALPHA,ALPHA-DIALKYL BETA-KETO-ESTERS HAVING EITHER (R)-CHIRAL OR (S)-CHIRAL QUATERNARY CENTER DEPENDING ON THE SOLVENT SYSTEM
ANDO, K
TAKEMASA, Y
TOMIOKA, K
KOGA, K
[J]. TETRAHEDRON, 1993, 49 (08) : 1579 - 1588
[2] NEW ROUTE TO (-)-FRONTALIN AND (-)-MALYNGOLIDE VIA EPOXYKETONE REARRANGEMENT
ASAOKA, M
HAYASHIBE, S
SONODA, S
TAKEI, H
[J]. TETRAHEDRON, 1991, 47 (34) : 6967 - 6974
[3] CONSTRUCTION OF CHIRAL QUARTERNARY CARBON CENTERS USING 3-SUBSTITUTED 5-TRIMETHYLSILYL-2-CYCLOHEXENONES - SYNTHESIS OF (+)-ALPHA-CUPARENONE
ASAOKA, M
TAKENOUCHI, K
TAKEI, H
[J]. TETRAHEDRON LETTERS, 1988, 29 (03) : 325 - 328
[4] LACTONE FORMATION VIA OXIDATIVE CYCLIZATION OF AN UNSATURATED CARBOXYLIC-ACID - APPLICATION TO THE STEREOSELECTIVE SYNTHESIS OF (+/-)-MALYNGOLIDE, AN ANTIBIOTIC FROM THE MARINE BLUE-GREEN-ALGA LYNGBYA-MAJUSCULA GOMONT
BABLER, JH
INVERGO, BJ
SARUSSI, SJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (21) : 4241 - 4243
[5] SYNTHESIS OF MALYNGOLIDE, AN ANTIBIOTIC FROM THE MARINE BLUE-GREEN-ALGA LYNGBYA-MAJUSCULA GOMONT
CARDILLO, G
ORENA, M
PORZI, G
SANDRI, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (12) : 2439 - 2442
[6] STRUCTURE AND ABSOLUTE-CONFIGURATION OF MALYNGOLIDE, AN ANTIBIOTIC FROM THE MARINE BLUE-GREEN-ALGA LYNGBYA-MAJUSCULA GOMONT
CARDLLINA, JH
MOORE, RE
ARNOLD, EV
CLARDY, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (23) : 4039 - 4042
[7] PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES
COREY, EJ
VENKATESWARLU, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) : 6190 - +
[8] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS
DALE, JA
MOSHER, HS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) : 512 - 519
[9] ENANTIOSELECTIVE SYNTHESIS OF POLYFUNCTIONAL SMALL BUILDING-BLOCKS WITH A QUATERNARY STEREOGENIC CENTER
ENDERS, D
ZAMPONI, A
SCHAFER, T
NUBLING, C
EICHENAUER, H
DEMIR, AS
RAABE, G
[J]. CHEMISCHE BERICHTE, 1994, 127 (09) : 1707 - 1721
[10] DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF POLYFUNCTIONAL KETONES WITH ADJACENT QUATERNARY AND TERTIARY CENTERS BY ASYMMETRIC CARROLL REARRANGEMENT
ENDERS, D
KNOPP, M
RUNSINK, J
RAABE, G
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (20): : 2278 - 2280

← 1 2 3 4 5 →