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Convergent and Stereoselective Synthesis of Sarcophytol‐Q Precursor: (11 S )‐3,7,11,15‐Tetramethyl‐11‐hydroxy‐14‐oxo‐3 E ,7 E ,12 E ‐hexadecatrienal
Author(s) -
Li WeiDong,
Li YuLin,
Li Ying
Publication year - 1995
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.199500094
Subject(s) - chemistry , dehydrohalogenation , allylic rearrangement , stereoselectivity , sulfone , geraniol , catalysis , chloride , stereochemistry , epoxide , sharpless epoxidation , medicinal chemistry , organic chemistry , chromatography , essential oil
A chiral precursor of sarcophytol‐Q, (11S)‐3,7,11,15‐tetramethyl‐11‐hydroxy‐14‐oxo‐3E,7E,12E‐hexadecatrienal, was synthesized in a convergent and stereoselective manner starting from geraniol and 4‐hydroxy‐2‐butanone in nine steps. The key steps were asymmetric Sharpless epoxidation, base‐induced dehydrohalogenation rearrangement of chiral epoxy chloride 5 and the phase transfer catalytic coupling reaction of allylic phenyl sulfone 4 with chiral allylic chloride 3 .