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Stereoselective Total Synthesis of (3 S ,5 S )‐1,7‐Bis(4‐hydroxyphenyl)heptane‐3,5‐diol, (3 S ,5 S )‐Alpinikatin, and Its Diastereoisomers
Author(s) -
Venkatesham Kunuru,
Purushotham Reddy Sudina,
Chinnababu Baggu,
Suresh Babu Katragadda
Publication year - 2015
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.201500073
Subject(s) - chemistry , stereoselectivity , diastereomer , diol , heptane , total synthesis , stereochemistry , alkynylation , diarylheptanoids , organic chemistry , catalysis
Stereoselective synthesis of the diarylheptanoids, (3 S ,5 S )‐1,7‐bis(4‐hydroxyphenyl)heptane‐3,5‐diol ( 1 ), (3 S ,5 S )‐alpinikatin ( 3 ), and their diastereoisomers ( 2 and 4 , resp.), was achieved from readily available 4‐hydroxybenzaldehyde. The synthetic sequences involve Browns 's allylation and Et 2 Zn mediated diastereoselective alkynylation reaction as key steps.