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Org Lett. 2012 Sep 7;14(17):4442-5. doi: 10.1021/ol3019456. Epub 2012 Aug 27.

Stereoselective synthesis of acortatarins A and B.

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1
Tri-Institutional Training Program in Chemical Biology, Memorial Sloan-Kettering Cancer Center, 1275 York Avenue, Box 422, New York, New York 10065, USA.

Abstract

Acortatarins A and B have been synthesized via stereoselective spirocyclizations of glycals. Mercury-mediated spirocyclization of a pyrrole monoalcohol side chain leads to acortatarin A. Glycal epoxidation and reductive spirocyclization of a pyrrole dialdehyde side chain leads to acortatarin B. Acid equilibration and crystallographic analysis indicate that acortatarin B is a contrathermodynamic spiroketal with distinct ring conformations compared to acortatarin A.

PMID:
22924668
PMCID:
PMC3466107
DOI:
10.1021/ol3019456
[Indexed for MEDLINE]
Free PMC Article
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