Convergent synthesis of the IJKLM-ring part of ciguatoxin CTX3C |
| |
Authors: | Daisuke Domon Akio Murai Hidethoshi Kawai Takanori Suzuki |
| |
Institution: | Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan |
| |
Abstract: | Convergent synthesis of the IJKLM-ring part (2) of ciguatoxin CTX3C has been achieved from the I-ring and the L-ring parts (4 and 5) in total eight steps in 27% overall yield. The carbanion derived from 4, stabilized by a dimethyldithioacetal S-oxide group, was readily reacted with aldehyde 5 to give an adduct, which was facilely transformed into the corresponding α,ε-dihydroxy ketone 3. The JK-ring formation from 3 under reductive conditions followed by oxidative M-ring cyclization efficiently led to the pentacyclic ether 2. Improved synthesis of 6, a synthetic intermediate for 4, was also established. |
| |
Keywords: | Ciguatoxin CTX3C Natural product synthesis Acyl anion equivalent Reductive etherification Spirocyclic acetal formation |
本文献已被 ScienceDirect 等数据库收录! |
|