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
收藏
页码：3970 / 3973
页数：4
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