Direct Oxa-Pictet-Spengler Cyclization to the Natural (3a,5)-trans-Stereochemistry in the Syntheses of (+)-7-Deoxyfrenolicin B and (+)-7-Deoxykalafungin

被引：34

作者：

Eid, Clark N. ^{[1
]}

Shim, Jaechul ^{[1
]}

Bikker, Jack ^{[1
]}

Lin, Melissa ^{[1
]}

机构：

[1] Wyeth Res, Chem & Screening Sci, Pearl River, NY 10965 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 01期

关键词：

CATALYZED ASYMMETRIC DIHYDROXYLATION; ANTIBIOTICS;

D O I：

10.1021/jo801945n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The pyranonaphthoquinones (+)-7-deoxyfrenolicin B and (+)-7-deoxykalafungin were synthesized in four steps using an oxa-Pictet-Spengler cyclization that directly provided the natural (3a,5)-trans-substituted dihydronaphthopyrans with high diastereoselectivity. This outcome is in contrast to the unnatural (3a,5)-cis-substituted dihydronaphthopyrans reported under similar conditions for the syntheses of (+)frenolicin B and (+)-kalafungin. Computational modeling is presented that provides insight into this unusual stereoselectivity.

引用

页码：423 / 426

页数：4

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