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Studies on macrocyclic diterpenoids. V. Synthesis of (±)‐sarcophytol‐A benzyl ether
Author(s) -
Li WeiDong,
Li Ying,
Mao JianMin,
Li YuLin
Publication year - 1993
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.19930110209
Subject(s) - chemistry , allylic rearrangement , ether , geraniol , acetone , catalysis , coupling reaction , organic chemistry , williamson ether synthesis , formal synthesis , phase transfer catalyst , medicinal chemistry , combinatorial chemistry , chromatography , essential oil
The title compound, sarcophytol‐A benzyl ether has been synthesized through 13 steps by employing acetone and geraniol as starting materials. The key steps in the synthesis were double bond migration reaction of allylic alcohols 5 and 6, phase transfer catalytic coupling (PTC) reaction of II with 7 and the cyclization reaction of dicarbonyl acyclic precursor induced by TiCl 3 ‐AlCl 3 (3:1)/Zn‐Cu system.