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Stereoselective Total Synthesis of Natural (S)-Bakuchiol and Its Enantiomer

✍ Scribed by Xiao-Long Du; Hong-Li Chen; Hui-Jin Feng; Yuan-Chao Li

Publisher: John Wiley and Sons
Year: 2008
Tongue: German
Weight: 233 KB
Volume: 91
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.200890041

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✦ Synopsis

Abstract

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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