4.8 Article

Ring-Contraction vs Ring-Expansion Reactions of Spiro-cyclopropanecarboxylated Sugars

Journal

ORGANIC LETTERS
Volume 15, Issue 17, Pages 4474-4477

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol402021e

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Funding

  1. Council of Scientific and Industrial Research (CSIR), New Delhi [01(2408)/10/EMR-II]

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Electrophilic ring opening of spiro-cyclopropanecarboxylated sugars followed by reaction with DBU revealed interesting ring-contraction and ring-expansion reactions depending on the substrate and the kind of hydroxyl protective group present adjacent to the Spiro center. A stereoselective method for accessing a new class of carbon chain extended keto-furanoses and C-glycosylated bicyclic compounds is reported.

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