930803-84-2Relevant academic research and scientific papers
Synthesis of moenocinol and its analogs using BT-sulfone in Julia-Kocienski olefination
Huang, Hung-Jyun,Yang, Wen-Bin
, p. 1429 - 1433 (2008/02/02)
Moenocinol (C25H42O), the acyclic terpenoid unsaturated lipid part of moenomycin antibiotics, was prepared by an expedient method, which comprised organometallic reaction, Julia-Kocienski olefination, and enolate carbon bond formation as the key steps. The starting materials, nerol and 3-butyn-1-ol, were elaborated to the benzothiazole sulfone 2 and aldehyde 3, and the subsequent Julia-Kocienski olefination occurred in a stereospecific manner to give the desired 6E-configuration of moenocinol. Moenocinol (1) was thus synthesized by 10 linear steps in 12% overall yield, and its analogs 23, 24, and 28 with different chain lengths and unsaturation degrees were also realized by the similar reaction sequences.
