Bioinspired Total Synthesis and Stereochemical Revision of the Fungal Metabolite Pestalospirane B.

Sandhya BadrinarayananChristopher J SquireJonathan Sperry Margaret A Brimble

Published in: Organic letters (2017)

The total synthesis of both enantiomers of pestalospirane B, 2, has been achieved using a bioinspired tandem dimerization-spiroketalization reaction. Electronic circular dichroism (ECD) and X-ray analysis were used to revise the absolute stereochemistry of the natural product pestalospirane B from 3S, 3'S, 12R, 12'R to its enantiomer 3R, 3'R, 12S, 12'S.

Keyphrases

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