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Synthesis of Racemic Δ 3 ‐2‐Hydroxybakuchiol and Its Analogues
Author(s) -
Shi Lei,
Lei Xinsheng,
Zhang Jiange,
Lin Guoqiang
Publication year - 2010
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.200900243
Subject(s) - chemistry , negishi coupling , stereochemistry , phenol , iodide , medicinal chemistry , organic chemistry , catalysis
The first synthetic approach to (±)‐Δ 3 ‐2‐hydroxybakuchiol (=4‐[(1 E ,5 E )‐3‐ethenyl‐7‐hydroxy‐3,7‐dimethylocta‐1,5‐dien‐1‐yl]phenol; 14 ) and its analogues 13a – 13f was developed by 12 steps ( Schemes 2 and 3 ). The key features of the approach are the construction of the quaternary C‐center bearing the ethenyl group by a Johnson–Claisen rearrangement (→ 6 ); and of an ( E )‐alkenyl iodide via a Takai–Utimoto reaction (→ 11 ); and an arylation via a Negishi cross‐coupling reaction (→ 12e – 12f ).
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