STEREOSELECTIVE SYNTHESIS OF SYN-1,3-DIOLS

被引：18

作者：

MOHR, P

机构：

[1] Pharmaceutical Research Department, F. Hoffmann-La Roche Ltd

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 18期

关键词：

EPOXIDATION; SYN-1,3-DIOL; PIG LIVER ESTERASE;

D O I：

10.1016/S0040-4039(00)92213-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Z-allylsilanes 1 are epoxidized by V5+/TBHP with high erythro-selectivity (up to 97:3) . HF- or TBAF-induced fragmentation leads to syn-1,3-diols 3. Compound 3f can be transformed within two steps into a key synthon for the lactone moiety of compactin.

引用

收藏

页码：2455 / 2458

页数：4

相关论文

共 13 条

[1] SYNTHESES OF 4(R)-SILYLOXY-6(S)-IODOMETHYL-TETRAHYDROPYRAN-2-ONE AND ITS ENANTIOMER, BUILDING-BLOCKS FOR HMG-COA REDUCTASE INHIBITORS [J].

BAADER, E ;

BARTMANN, W ;

BECK, G ;

BERGMANN, A ;

FEHLHABER, HW ;

JENDRALLA, H ;

KESSELER, K ;

SARIC, R ;

SCHUSSLER, H ;

TEETZ, V ;

WEBER, M ;

WESS, G .

TETRAHEDRON LETTERS, 1988, 29 (21) :2563-2566

[2]

BONINI C, 1991, GAZZ CHIM ITAL, V121, P75

[3] DIASTEREOSELECTION IN THE ADDITION OF ENOLATES TO CHIRAL ALPHA,BETA-EPOXYALDEHYDES [J].

ESCUDIER, JM ;

BALTAS, M ;

GORRICHON, L .

TETRAHEDRON LETTERS, 1991, 32 (39) :5345-5348

[4]

JEWELL CF, 1986, Patent No. 4625039

[5] VANADIUM-CATALYZED EPOXIDATIONS .2. HIGHLY STEREOSELECTIVE EPOXIDATIONS OF ACYCLIC HOMOALLYLIC ALCOHOLS PREDICTED BY A DETAILED TRANSITION-STATE MODEL [J].

MIHELICH, ED ;

DANIELS, K ;

EICKHOFF, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (25) :7690-7692

[6] STEREOSELECTIVE SYNTHESIS OF FUNCTIONALIZED ERYTHRO/1,3-DIOLS [J].

MOHR, P ;

TAMM, C .

TETRAHEDRON LETTERS, 1987, 28 (04) :391-394

[7] KINETIC RESOLUTION OF RACEMIC BETA,GAMMA-EPOXY ESTERS WITH PIG-LIVER ESTERASE (PLE, EC 3.1.1.1.) [J].

MOHR, P ;

ROSSLEIN, L ;

TAMM, C .

TETRAHEDRON LETTERS, 1989, 30 (19) :2513-2516

[8] TOTAL SYNTHESIS OF AMPHOTERONOLIDE-B AND AMPHOTERICIN-B .1. STRATEGY AND STEREOCONTROLLED CONSTRUCTION OF KEY BUILDING-BLOCKS [J].

NICOLAOU, KC ;

DAINES, RA ;

UENISHI, J ;

LI, WS ;

PAPAHATJIS, DP ;

CHAKRABORTY, TK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (14) :4672-4685

[9]

OISHI T, 1991, J ORG CHEM, V56, P741

[10]

Pirkle W.H., 1982, TOP STEREOCHEM, V13, P263