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Stereoselective Total Synthesis of Natural ( S )‐Bakuchiol and Its Enantiomer
Author(s) -
Du XiaoLong,
Chen HongLi,
Feng HuiJin,
Li YuanChao
Publication year - 2008
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200890041
Subject(s) - chemistry , geraniol , enantiomer , stereoselectivity , silylation , stereochemistry , aldehyde , total synthesis , enantioselective synthesis , organic chemistry , catalysis , chromatography , essential oil
A practical stereoselective synthesis of ( S )‐bakuchiol ( 1 ) and its enantiomer is reported. The important intermediate, ( R )‐configured β ‐siloxy aldehyde 5 , was obtained in three steps from the easily available material geraniol ( 2 ) via the key step of Yamamoto 's rearrangement of epoxy silyl ethers. ( S )‐Bakuchiol ( 1 ) and its enantiomer, ( R )‐bakuchiol ( 17 ), were finally obtained in different synthetic sequences with overall yields of 51% (ten steps) and 40% (nine steps) from geraniol ( 2 ), respectively.