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Chiroptical properties and synthesis of enantiopure cis and trans Pterocarpan Skeleton
Author(s) -
Kiss Loránd,
Kurtán Tibor,
Antus Sándor,
Bényei Attila
Publication year - 2003
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.10235
Subject(s) - chemistry , enantiopure drug , enantioselective synthesis , stereochemistry , catalysis , organic chemistry
Abstract The first enantioselective synthesis of trans ‐(6a S, 11a R )‐pterocarpan [(+)‐ 2 ] and its conversion to cis ‐(6a S, 11a S )‐pterocarpan [(+)‐ 1 ] was achieved starting from racemic 2′‐benzyloxyflavanone ( rac ‐ 3 ). Their stereochemistry was deduced by X‐ray analysis of the ketal intermediate (–)‐ 5a. The CD study of (+)‐ 1 and (+)‐ 2 allows the configurational assignment of similar pterocarpan derivatives by CD spectroscopy. Chirality 15:558–563, 2003. © 2003 Wiley‐Liss, Inc.