Organic Letters 2001-10-04

An aldol-based approach to the asymmetric synthesis of L-callipeltose, the deoxyamino sugar of L-callipeltoside A.

D A Evans, E Hu, J S Tedrow

Index: Org. Lett. 3(20) , 3133-6, (2001)

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Abstract

[reaction: see text] The L-callipeltose subunit of L-callipeltoside A has been synthesized in 10 steps and 13% overall yield from D-threonine. The key steps are a highly diastereoselective Felkin anti aldol addition to a methyl ketone and a selective methylation of a secondary alcohol in the presence of a secondary carbamate.