Stereoselective Total Synthesis of Natural ( S )‐Bakuchiol and Its Enantiomer | Zendy

Du XiaoLong | Zendy; Chen HongLi | Zendy; Feng HuiJin | Zendy; Li YuanChao | Zendy

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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.

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