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J Am Chem Soc. 2013 Jan 30;135(4):1209-12. doi: 10.1021/ja310778t. Epub 2013 Jan 11.

Synthesis of (-)-neothiobinupharidine.

Author information

1
Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.

Abstract

An eight step, asymmetric synthesis of a dimeric thiaspirane nuphar alkaloid from 3-methyl-2-cyclo-pentenone is reported. The brevity of the route relies on a useful procedure for tandem reductive allylation of cyclopentenones, as well as the minimization of redox manipulations and other functional group interconversions. The distribution of products that arise from spontaneous dimerization points to a more complex biosynthesis.

PMID:
23298203
DOI:
10.1021/ja310778t
[Indexed for MEDLINE]

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