Journal
CHEMICAL SCIENCE
Volume 3, Issue 6, Pages 1798-1803Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2sc20270k
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Funding
- NIH-NIGMS [GM089732]
- Amgen
- NSF [CHE-0946721]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [946721] Funding Source: National Science Foundation
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The first total synthesis of (+)-gliocladin B is described. Our concise and enantioselective synthesis takes advantage of a new regioselective Friedel-Crafts-based strategy to provide an efficient multigram-scale access to the C3-(3'-indolyl)hexahydropyrroloindole substructure, a molecular foundation present in a significant subset of epipolythiodiketopiperazine natural alkaloids. Our first-generation solution to (+)-gliocladin B involved the stereoselective formation of (+)-12-deoxybionectin A, a plausible biosynthetic precursor. Our synthesis clarified the C15 stereochemistry of (+)-gliocladin B and allowed its full structure confirmation. Further studies of a versatile dihydroxylated diketopiperazine provided a concise and efficient synthesis of (+)-gliocladin B as well as access to (+)-gliocladin C.
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