Toward the Total Synthesis of Amphidinolide N: Synthesis of the C8-C29 Fragment

被引:11
|
作者
Kawashima, Yuki [1 ]
Toyoshima, Atsushi [1 ]
Fuwa, Haruhiko [1 ]
Sasaki, Makoto [1 ]
机构
[1] Tohoku Univ, Grad Sch Life Sci, Aoba Ku, 2-1-1 Katahira, Sendai, Miyagi 9808577, Japan
基金
日本学术振兴会;
关键词
CARIBENOLIDE-I STRUCTURES; SECONDARY ALCOHOLS; OLEFIN METATHESIS; ANTITUMOR MACROLIDE; SELECTIVE OXIDATION; PROPOSED STRUCTURE; DIRECT CONVERSION; ENOL ETHERS; RING; STRATEGY;
D O I
10.1021/acs.orglett.6b00871
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A synthesis of the C8-C29 fragment of amphidinolide N, a potent cytotoxic macrolide isolated from the marine dinoflagellate Amphidinium sp., has been achieved. The key features of the synthesis involve a convergent union of the C9-C15 and C16-C29 fragments by Steglich esterification and the construction of a pyran unit through a Tebbe methylenation/ring-closing metathesis sequence.
引用
收藏
页码:2232 / 2235
页数:4
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