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Stereoselective synthesis of ( Z )‐5‐(Trideca‐4‐enyl)resorcinol and gibbilimbols A—D
Author(s) -
Zhou Ling,
Li Yang,
Cao XiaoPing
Publication year - 2004
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.20040221126
Subject(s) - chemistry , resorcinol , anhydrous , wittig reaction , phosphonium , stereoselectivity , potassium , alkyl , medicinal chemistry , organic chemistry , catalysis
( Z )‐5–(Trideca‐4‐enyl)resorcinol (1) and gibbilimbols A—D (2–5) were synthesized in 47%‐60% yields over 6 steps from commercially available starting materials. The Wittig reaction of various alkyl phosphonium bromides with appropriate aldehydes in the presence of potassium ten‐butoxide ( t ‐BuOK) in anhydrous THF solution at room temperature served as the key step, and the result showed that only (Z)‐configuration olefins were formed by this procedure. The synthesis of the ( Z )‐5‐(trideca‐4‐enyl)resorcinol (1) was reported for the first time.