Convergent synthesis of the ABCDE-ring part of ciguatoxin CTX3C |
| |
Authors: | Kenshu Fujiwara Hidetoshi Kawai Takanori Suzuki |
| |
Affiliation: | Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan |
| |
Abstract: | Convergent synthesis of the ABCDE-ring part (2) of ciguatoxin CTX3C (1) has been achieved. A carbanion stabilized by a dimethyldithioacetal S-oxide group in the AB-ring part (4) readily reacted with an aldehyde group in the E-ring part (5). The resulting adduct was facilely converted to the corresponding β,γ-unsaturated α,ε-dihydroxy ketone (3). The subsequent reductive hydroxy-ketone-cyclization reactions constructed the CD-ring part efficiently. Thus, the ABCDE-ring part (2) was concisely synthesized in 10 steps in 11% overall yield from the AB-ring and the E-ring parts (4 and 5). |
| |
Keywords: | Polyether Ciguatoxin CTX3C Natural product synthesis Acyl anion equivalent Convergent synthesis |
本文献已被 ScienceDirect 等数据库收录! |