Concise total synthesis of (+)-gliocladins B and C
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Movassaghi_Concise total.pdf
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Author(s)
Movassaghi, Mohammad
Boyer, Nicolas Cedric
Date Issued
March 2012
Journal
Chemical Science
Publisher
Royal Society of Chemistry, The
Citation
Boyer, Nicolas, and Mohammad Movassaghi. “Concise total synthesis of (+)-gliocladins B and C.” Chemical Science 3, no. 6 (2012): 1798.
Version
Author's final manuscript
Abstract
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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Creative Commons Attribution-Noncommercial-Share Alike 3.0
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DOI of Published Version
https://doi.org/10.1039/c2sc20270k
