Jump to main content
Jump to site search

Issue 18, 2004
Previous Article Next Article

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

Author affiliations

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.

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

Back to tab navigation

Publication details

The article was received on 02 Apr 2004, accepted on 02 Aug 2004 and first published on 24 Aug 2004


Article type: Paper
DOI: 10.1039/B404962D
Citation: Org. Biomol. Chem., 2004,2, 2630-2649
  •   Request permissions

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

    S. G. Davies, J. R. Haggitt, O. Ichihara, R. J. Kelly, M. A. Leech, A. J. Price Mortimer, P. M. Roberts and A. D. Smith, Org. Biomol. Chem., 2004, 2, 2630
    DOI: 10.1039/B404962D

Search articles by author

Spotlight

Advertisements