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

Badrinarayanan, Sandhya; Squire, Christopher J.; Sperry, Jonathan; Brimble, Margaret A.

doi:10.1021/acs.orglett.7b01371.s001

ol7b01371_si_001.pdf (2.63 MB)

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

journal contribution

posted on 2017-06-16, 18:18 authored by Sandhya Badrinarayanan, Christopher J. Squire, Jonathan Sperry, Margaret A. Brimble

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.