Total Synthesis of the Proposed Structure of Didemnaketal B

被引：13

作者：

Fuwa, Haruhiko ^{[1
]}

Sekine, Kumiko ^{[1
]}

Sasaki, Makoto ^{[1
]}

机构：

[1] Tohoku Univ, Gradutate Sch Life Sci, Aoba Ku, Sendai, Miyagi 9808577, Japan

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 15期

基金：

日本学术振兴会;

关键词：

PROTEASE INHIBITIVE DIDEMNAKETALS; CROSS-COUPLING REACTIONS; HIV-1; PROTEASE; STEREOCONTROLLED SYNTHESIS; ABSOLUTE-CONFIGURATION; CONVERGENT SYNTHESIS; ALDEHYDES; SUBUNIT; ACETALS; CORE;

D O I：

10.1021/ol4017518

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Total synthesis of the proposed structure of didemnaketal B has been accomplished. The C7-C21 spiroacetal domain was synthesized by exploiting our Suzuki-Miyaura coupling/spiroacetalization strategy. The C1-C7 acyclic domain was constructed via an Evans syn-aldol reaction and a vinylogous Mukaiyama aldol reaction. Finally, the C22-C28 side chain was introduced by means of a Nozaki-Hiyama-Kishi reaction. Comparison of the NMR spectroscopic data of our synthetic material with those of the authentic sample revealed that the proposed structure requires stereochemical reassignment.

引用

页码：3970 / 3973

页数：4

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