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Diastereoselective conjugate addition of homochiral lithium (R)-N-allyl-N-alpha-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 publication

DOI

10.1039/B404962D

Type

Journal article

Journal

Org Biomol Chem

Publication Date

21/09/2004

Volume

2

Pages

2630 - 2649

Keywords

Amides, Amidines, Anti-Bacterial Agents, Lithium, Models, Molecular, Molecular Structure, Organometallic Compounds