10.1021/acs.orglett.7b01371.s001
Sandhya Badrinarayanan
Sandhya
Badrinarayanan
Christopher J. Squire
Christopher J.
Squire
Jonathan Sperry
Jonathan
Sperry
Margaret A. Brimble
Margaret A.
Brimble
Bioinspired Total Synthesis and Stereochemical Revision
of the Fungal Metabolite Pestalospirane B
American Chemical Society
2017
dichroism
ECD
Stereochemical Revision
X-ray analysis
Fungal Metabolite Pestalospirane B
12 S
stereochemistry
pestalospirane B
synthesis
dimerization
Bioinspired
3 S
bioinspired
12 R
enantiomer 3 R
tandem
product pestalospirane B
Synthesi
Electronic
2017-06-16 18:18:42
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Bioinspired_Total_Synthesis_and_Stereochemical_Revision_of_the_Fungal_Metabolite_Pestalospirane_B/5116198
The total synthesis
of both enantiomers of pestalospirane B, <b>2</b>, 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 3<i>S</i>, 3′<i>S</i>, 12<i>R</i>, 12′<i>R</i> to its enantiomer
3<i>R</i>, 3′<i>R</i>, 12<i>S</i>, 12′<i>S</i>.