The first enantioselective synthesis of trans-(6aS,11aR)-pterocarpan [(+)-2] and its conversion to cis-(6aS,11aS)-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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Volume15, Issue6

2003

Pages 558-563

Chiroptical properties and synthesis of enantiopure cis and trans Pterocarpan Skeleton

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Chiroptical properties and synthesis of enantiopure cis and trans Pterocarpan Skeleton

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