Synthesis of the Bis-tetrahydropyran Core of Amphidinol 3

被引：31

作者：

Crimmins, Michael T. ^{[1
]}

Martin, Timothy J. ^{[1
]}

Martinot, Theodore A. ^{[1
]}

机构：

[1] Univ N Carolina, Kenan & Caudill Labs Chem, Chapel Hill, NC 27599 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 17期

关键词：

STEREOSELECTIVE-SYNTHESIS; FRAGMENT; EFFICIENT; REDUCTION; ACCESS;

D O I：

10.1021/ol1015898

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convergent synthesis of the C31-C52 bis-tetrahydropyran core of the natural product amphidinol 3 is reported. A common intermediate was synthesized from D-tartaric acid utilizing an asymmetric glycolate alkylation/ring-closing metathesis sequence to construct the THP rings. Differential elaboration of the common intermediate allowed the synthesis of two distinct coupling partners which were joined through a modified Horner-Wadsworth-Emmons olefination to provide the bis-tetrahydropyran core.

引用

页码：3890 / 3893

页数：4

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