Synthesis of carbasugar derivatives via a "Pseudo"-C2-symmetric building block derived from arabitol

Abstract

Development of a kinetic protection protocol for arabitol affords the "pseudo"-C2- symmetric bis-acetal 8 in good yield. Utilising a scavenging purification strategy greatly simplifies the separation of 8 from the thermodynamically more stable regioisomeric byproduct 7. The building block 8 is utilised in a series of syntheses to yield a "pseudo"-C2- symmetric and C2-symmetric 1,4-bis-epoxides in 3 and 5 steps, respectively, from 8. These bis-epoxides are then reacted with a dithiane stabilised carbanion in a Brook rearrangement mediated cyclisation to furnish carbasugar derivatives in enantiopure form. The "pseudo"-C2-symmetric bis-epoxide gives a distereomeric mixture as expected, while the CVsymmetric bis-epoxide reacts to form only one diastereomer.

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