Asymmetric total synthesis of sperabillins B and D via lithium amide conjugate addition

Stephen G. Davies*, Jane R. Haggitt, Osamu Ichihara, Richard J. Kelly, Michael A. Leech, Anne J.Price Mortimer, Paul M. Roberts, Andrew D. Smith

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

50 Citations (Scopus)

Abstract

Diastereoselective conjugate addition of homochiral lithium (R)-N-allyl-N-α-methylbenzylamide to methyl (2E,5E)-hepatadienoate, followed by protecting group manipulation and subsequent iodocyclocarbamation allows a concise route to the core fragment, methyl (3R,5R,6R)-3,6-diamino-5- hydroxyheptanoate, of sperabillins B and D. Differentiation between the C-3 and C-6 primary amino groups of this core amino acid was readily achieved by treatment with acetone, giving the 5,6-isopropylidene and C-3-imine protected diamine, with subsequent regioselective acylation of the C-6-nitrogen facilitating the total synthesis of sperabillin D in 10.8% overall yield, and the first asymmetric synthesis of sperabillin B in 5.8% overall yield.

Original languageEnglish
Pages (from-to)2630-2649
Number of pages20
JournalOrganic and Biomolecular Chemistry
Volume2
Issue number18
DOIs
Publication statusPublished - 21 Sept 2004

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