ENANTIOSELECTIVE TOTAL SYNTHESIS OF (+)-BUCIDARASINS A AND C

被引：5

作者：

Usui, Kenji ^{[1
]}

Nakada, Masahisa ^{[1
]}

机构：

[1] Waseda Univ, Fac Sci & Engn, Dept Chem & Biochem, Shinjuku Ku, 3-4-1 Ohkubo, Tokyo 1698555, Japan

来源：

HETEROCYCLES | 2015年 / 91卷 / 02期

关键词：

Clerodane Diterpene; Diels-Alder Reaction; Enantioselective Synthesis; Natural Product; Total Synthesis; CYTOTOXIC CLERODANE DITERPENOIDS; CHIRAL BUILDING-BLOCKS; ANTITUMOR PRINCIPLES; CASEARIN X; LEAVES; TWIGS; BARK; FLACOURTIACEAE; DERIVATIVES; ROOTS;

D O I：

10.3987/COM-14-13161

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this paper, the first total synthesis of (+)-bucidarasins A and C is described. The chiral starting material was successfully obtained via reduction using a CBS catalyst and selective mono-TBS ether formation of trans-2-benzyloxymethy1-2-methylcyclohexane-1,3-diol, which was crucial to the successful enantioselective total synthesis of (+)-bucidarasins A and C. A synthetic approach towards (+)-bucidarasin C, based on the Barton-McCombie protocol, using V-70 as a radical promoter at low temperature to remove the C6-hydroxy moiety is also described.

引用

页码：332 / 350

页数：19

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