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Open Chain Chiral Macrolide Building Blocks by Opening of Deoxygenated 1,6-Anhydrosugars with 1,3-Propanedithiol
Journal article   Peer reviewed

Open Chain Chiral Macrolide Building Blocks by Opening of Deoxygenated 1,6-Anhydrosugars with 1,3-Propanedithiol

Karsten Krohn, Ishtiaq Ahmed, Dietmar Gehle, Mohammed Al Sahli and Mohammed Alsahli
Journal of carbohydrate chemistry, Vol.28(2), pp.64-77
27/02/2009
DOI: https://doi.org/10.1080/07328300802691851

Abstract

1,3-Dithianes 1,6-Anhydrosugars Chiral building blocks Ring opening with 1,3-propandithiol Černý epoxides
Chiral building blocks for macrolides and related natural products are obtained from 1,6-anhydrosugars by conversion of the bicyclic acetals 2 or 12 into the open chain chiral 1,3-dithianes 6 and 13. Branched precursors can be obtained by opening of the Černý epoxide 1 with the 1,3-dithiane anion to yield 7, followed by ring opening with 1,3-propanedithiol to the bis-1,3-dithiane 8.

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