A novel stereoselective synthesis of enantiomerically pure antifungal agent, (+)-preussin

被引:54
作者
Yoda, H
Yamazaki, H
Takabe, K
机构
[1] Department of Molecular Science, Faculty of Engineering, Shizuoka University
关键词
D O I
10.1016/0957-4166(96)00009-2
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
An efficient and novel process is described for the asymmetric synthesis of (2S,3S,SR)-1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinol, (+)-preussin employing reductive deoxygenation of a functionalized quaternary alpha-hydroxy N-Boc pyrrolidine obtained by stereocontrolled elaboration of tri-O-benzyl-beta-D-arabinofuranose. The synthetic strategy involves no separation of stereoisomers through the entire sequence.
引用
收藏
页码:373 / 374
页数:2
相关论文
共 12 条
[1]   SYNTHESIS APPLICATIONS OF CATIONIC AZA-COPE REARRANGEMENTS .27. ENANTIOSELECTIVE TOTAL SYNTHESIS OF EITHER ENANTIOMER OF THE ANTIFUNGAL ANTIBIOTIC PREUSSIN (L-657,398) FROM (S)-PHENYLALANINE [J].
DENG, W ;
OVERMAN, LE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (25) :11241-11250
[2]   A STEREOSELECTIVE SYNTHESIS OF A NOVEL MODEL-COMPOUND OF CARZINOPHILIN CARRYING THE C6-C-13 UNIT WITH CORRECT STEREOCHEMISTRY [J].
HASHIMOTO, M ;
TERASHIMA, S .
CHEMISTRY LETTERS, 1994, (06) :1001-1002
[3]   THE RELATIVE AND ABSOLUTE STEREOCHEMISTRY OF THE ANTIFUNGAL AGENT PREUSSIN [J].
JOHNSON, JH ;
PHILLIPSON, DW ;
KAHLE, AD .
JOURNAL OF ANTIBIOTICS, 1989, 42 (07) :1184-1185
[4]   A NEW PROCEDURE FOR THE SYNTHESIS OF AZASUGARS [J].
LAY, L ;
NICOTRA, F ;
PAGANINI, A ;
PANGRAZIO, C ;
PANZA, L .
TETRAHEDRON LETTERS, 1993, 34 (28) :4555-4558
[5]   SYNTHETIC APPLICATIONS OF IMIDOTITANIUM ALKYNE [2+2] CYCLOADDITIONS - A CONCISE, STEREOCONTROLLED TOTAL SYNTHESIS OF THE ANTIFUNGAL AGENT (+)-PREUSSIN [J].
MCGRANE, PL ;
LIVINGHOUSE, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (24) :11485-11489
[6]   A CONCISE SYNTHESIS OF THE ANTIFUNGAL AGENT (+)-PREUSSIN [J].
OVERHAND, M ;
HECHT, SM .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (17) :4721-4722
[7]   TOTAL SYNTHESIS OF (+)-PREUSSIN, A NOVEL ANTIFUNGAL AGENT [J].
PAK, CS ;
LEE, GH .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (03) :1128-1133
[8]   L-657,398, A NOVEL ANTIFUNGAL AGENT - FERMENTATION, ISOLATION, STRUCTURAL ELUCIDATION AND BIOLOGICAL PROPERTIES [J].
SCHWARTZ, RE ;
LIESCH, J ;
HENSENS, O ;
ZITANO, L ;
HONEYCUTT, S ;
GARRITY, G ;
FROMTLING, RA ;
ONISHI, J ;
MONAGHAN, R .
JOURNAL OF ANTIBIOTICS, 1988, 41 (12) :1774-1779
[9]   RAPID SYNTHESIS OF 5-O-(TERT-BUTYLDIPHENYLSILYL)-2-DEOXY-L-RIBONOLACTONE [J].
SHARMA, R ;
MARQUEZ, VE .
SYNTHETIC COMMUNICATIONS, 1994, 24 (13) :1937-1945
[10]  
SHIMAZAKI M, 1993, HETEROCYCLES, V36, P1823