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J Am Chem Soc. 2008 Dec 3;130(48):16295-309. doi: 10.1021/ja804659n.

Total synthesis of (+)-azaspiracid-1. An exhibition of the intricacies of complex molecule synthesis.

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  • 1Department of Chemistry & Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA. evans@chemistry.harvard.edu

Abstract

The synthesis of the marine neurotoxin azaspiracid-1 has been accomplished. The individual fragments were synthesized by catalytic enantioselective processes: A hetero-Diels-Alder reaction to afford the E- and HI-ring fragments, a carbonyl-ene reaction to furnish the CD-ring fragment, and a Mukaiyama aldol reaction to deliver the FG-ring fragment. The subsequent fragment couplings were accomplished by aldol and sulfone anion methodologies. All ketalization events to form the nonacyclic target were accomplished under equilibrating conditions utilizing the imbedded configurations of the molecule to adopt one favored conformation. A final fragment coupling of the anomeric EFGHI-sulfone anion to the ABCD-aldehyde completed the convergent synthesis of (+)-azaspiracid-1.

PMID:
19006391
[PubMed - indexed for MEDLINE]
PMCID:
PMC3408805
Free PMC Article
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