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Issue 18, 2004
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Asymmetric total synthesis of sperabillins B and D via lithium amide conjugate addition

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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

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Article information


Submitted
02 Apr 2004
Accepted
02 Aug 2004
First published
24 Aug 2004

Org. Biomol. Chem., 2004,2, 2630-2649
Article type
Paper

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

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