Chiroptical properties and synthesis of enantiopure  cis  and  trans  Pterocarpan Skeleton | Zendy

Kiss Loránd | Zendy; Kurtán Tibor | Zendy; Antus Sándor | Zendy; Bényei Attila | Zendy

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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

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.

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