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
收藏
页码：5805 / 5818
页数：14
相关论文
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 [J].
ANDO, K ;
TAKEMASA, Y ;
TOMIOKA, K ;
KOGA, K .
TETRAHEDRON, 1993, 49 (08) :1579-1588
[2]   NEW ROUTE TO (-)-FRONTALIN AND (-)-MALYNGOLIDE VIA EPOXYKETONE REARRANGEMENT [J].
ASAOKA, M ;
HAYASHIBE, S ;
SONODA, S ;
TAKEI, H .
TETRAHEDRON, 1991, 47 (34) :6967-6974
[3]   CONSTRUCTION OF CHIRAL QUARTERNARY CARBON CENTERS USING 3-SUBSTITUTED 5-TRIMETHYLSILYL-2-CYCLOHEXENONES - SYNTHESIS OF (+)-ALPHA-CUPARENONE [J].
ASAOKA, M ;
TAKENOUCHI, K ;
TAKEI, H .
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 [J].
BABLER, JH ;
INVERGO, BJ ;
SARUSSI, SJ .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (21) :4241-4243
[5]   SYNTHESIS OF MALYNGOLIDE, AN ANTIBIOTIC FROM THE MARINE BLUE-GREEN-ALGA LYNGBYA-MAJUSCULA GOMONT [J].
CARDILLO, G ;
ORENA, M ;
PORZI, G ;
SANDRI, S .
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 [J].
CARDLLINA, JH ;
MOORE, RE ;
ARNOLD, EV ;
CLARDY, J .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (23) :4039-4042
[7]   PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES [J].
COREY, EJ ;
VENKATESWARLU, A .
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 [J].
DALE, JA ;
MOSHER, HS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519
[9]   ENANTIOSELECTIVE SYNTHESIS OF POLYFUNCTIONAL SMALL BUILDING-BLOCKS WITH A QUATERNARY STEREOGENIC CENTER [J].
ENDERS, D ;
ZAMPONI, A ;
SCHAFER, T ;
NUBLING, C ;
EICHENAUER, H ;
DEMIR, AS ;
RAABE, G .
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 [J].
ENDERS, D ;
KNOPP, M ;
RUNSINK, J ;
RAABE, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (20) :2278-2280
12345