Convergent Synthesis of the WXYZA′B′C′D′E′F′ Ring Segment of Maitotoxin

被引：3

作者：

Umeno, Keitaro ^{[1
]}

Onoue, Hisaaki ^{[1
]}

Konoki, Keiichi ^{[2
]}

Torikai, Kohei ^{[1
]}

Yasuno, Yoko ^{[1
]}

Satake, Masayuki ^{[3
]}

Oishi, Tohru ^{[1
]}

机构：

[1] Kyushu Univ, Fac & Grad Sch Sci, Dept Chem, Nishi Ku, 744 Motooka, Fukuoka 8190395, Japan

[2] Tohoku Univ, Grad Sch Agr Sci, Aoba Ku, 468-1 Aramaki Aza Aoba, Sendai, Miyagi 9808572, Japan

[3] Univ Tokyo, Sch Sci, Dept Chem, Bunkyo Ku, 7-3-1 Hongo, Tokyo 1130033, Japan

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 2022年 / 95卷 / 02期

关键词：

Maitotoxin; WXYZA ' B ' C ' D ' E ' F ' ring; Convergent synthesis; INDUCED CA2+ INFLUX; STEREOCHEMICAL ASSIGNMENT; STEREOSELECTIVE-SYNTHESIS; BIOLOGICAL-ACTIVITY; CHEMICAL-SYNTHESIS; SYSTEM; CONSTRUCTION; CIGUATOXIN; CONFIGURATION; STRATEGY;

D O I：

10.1246/bcsj.20210397

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Synthesis of the WXYZA'B'C'D'E'F' ring segment of maitotoxin, a ladder-shaped polyether produced by the dino-flagellate Gambierdiscus toxicus, was achieved based on a convergent strategy via a-cyano ethers developed in our laboratory. The WXYZ ring aldehyde and the C'D'E'F' diol were combined through the construction of the B' ring via ring-closing metathesis and the A' ring via O,S-acetal formation followed by radical reduction. Introduction of a terminal olefin in the side chain culminated in the convergent synthesis of the WXYZA'B'C' D'E'F' ring segment in 16 steps.

引用

页码：325 / 330

页数：6

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