HIGHLY STEREOSELECTIVE ACCESS TO NOVEL 2,2,4-TRISUBSTITUTED TETRAHYDROFURANS BY HALOCYCLIZATION - PRACTICAL CHEMOENZYMATIC SYNTHESIS OF SCH-51048, A BROAD-SPECTRUM ORALLY-ACTIVE ANTIFUNGAL AGENT

被引：33

作者：

SAKSENA, AK ^{[1
]}

GIRIJAVALLABHAN, VM ^{[1
]}

LOVEY, RG ^{[1
]}

PIKE, RE ^{[1
]}

WANG, HY ^{[1
]}

GANGULY, AK ^{[1
]}

MORGAN, B ^{[1
]}

ZAKS, A ^{[1
]}

PUAR, MS ^{[1
]}

机构：

[1] BIOTRANSFORMAT GRP,UNION,NJ 07083

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 11期

关键词：

D O I：

10.1016/0040-4039(95)00143-Z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient synthesis of (-)-(2R)-cis-tosylate 2 is reported via stereoselective 5-exo iodocyclization of the optically active 2,2-disubstituted olefin 9a. Enzymatic desymmetrization of the homoallylic diol 4 with Novo SP435 allowed optimal pro-(S) selectivity to provide the desired (-)-(S)-monoacetate 9a. Under the irreversible reaction conditions, the presence of a bulky aryl substituent on the 2,2-disubstituted olefin seems to determine stereochemical outcome of these halocyclizations.

引用

页码：1787 / 1790

页数：4

共 14 条

[1]

Bartlett P. A., 1984, ASYMMETRIC SYNTHESIS, V3, P411

[2]

BOLAND W, 1991, SYNTHESIS-STUTTGART, P1049

[3] STEREOCONTROLLED CYCLOFUNCTIONALIZATIONS OF DOUBLE-BONDS THROUGH HETEROCYCLIC INTERMEDIATES [J].