NEW, EFFICIENT, AND HIGH-YIELDING ASYMMETRIC SYNTHESIS OF (4S,5S)-CYTOXAZONE

被引：3

作者：

Babu, Kollapudi Chandra ^{[1
,2
]}

Reddy, Rapolu Naveen ^{[1
]}

Rao, Salluri Yellamanda ^{[1
]}

Venkateshwarlu, Palnati ^{[1
]}

Madhusudhan, Gutta ^{[1
]}

机构：

[1] Inogent Labs Private Ltd, Dept Res & Dev, Hyderabad, Andhra Pradesh, India

[2] Jawaharlal Nehru Technol Univ, Inst Sci & Technol, Ctr Pharmaceut Sci, Hyderabad, Andhra Pradesh, India

来源：

SYNTHETIC COMMUNICATIONS | 2012年 / 42卷 / 17期

关键词：

Chiral N-sulfinimine; (R)-glyceraldehyde acetonide; (4R5R)-cytoxazone; (4S5S)-cytoxazone; stereoselective 1,2-addition; IMINO 1,2-WITTIG REARRANGEMENT; STEREOSELECTIVE-SYNTHESIS; CYTOKINE MODULATOR; (-)-CYTOXAZONE; CYTOXAZONE; ROUTE;

D O I：

10.1080/00397911.2011.563450

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new approach for the asymmetric synthesis of (4S,5S)-cytoxazone 1 in five steps and in 48% overall yield starting from commercially available (R)-epichlorohydrin has been described. The key step include stereoselective 1,2-addition of p-methoxyphenyl magnesium bromide (p-OMePhMgBr) to chiral N-sulfinimine derived from (R)-glyceraldehyde acetonide and (S)-t-BSA, which gave corresponding sulfinamide 2 with high diastereoselectivity. Deprotection of the t-butylsulfonyl group and 1,3-dimethyl acetal in a single step followed by N-Boc protection and subsequent carbonylation yields the targeted (4S,5S)-cytoxazone 1.

引用

页码：2624 / 2631

页数：8

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