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J Org Chem. 2012 Oct 19;77(20):9357-60. doi: 10.1021/jo301465z. Epub 2012 Oct 3.

A protecting-group-free synthesis of Hagen's gland lactones.

Author information

1
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400 076, Maharashtra, India. rfernand@chem.iitb.ac.in

Abstract

A practical protecting group free synthesis of Hagen's gland lactones 1 and 2 is accomplished in four steps and 25.6 and 37.4% overall yields, respectively. The strategy relies on a one-pot conversion of D-glucono-δ-lactone to β-hydroxy-γ-vinyl-γ-lactone, cross-metathesis, and iodocyclization-deiodinization as key steps.

PMID:
23009058
DOI:
10.1021/jo301465z
[Indexed for MEDLINE]
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