Facile Enantiospecific Synthesis of Dihydroconduritols E and F

Abstract

An enantiospecific synthesis of cyclohexane-1,2,3,4-tetrols was accomplished from l-(+)-tartaric acid. Pivotal steps in the synthetic sequence include zinc-mediated Boord-type fragmentation of an acetonide, ring-closing metathesis (RCM), and osmium-mediated dihydroxylation.

Key words

cyclitols - ring-closing metathesis - tartaric acid - Boord fragmentation

References

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14

Stereochemistry of 18 was further proved by X-ray crystal structure analysis. (The crystallographic data has been deposited with The Cambridge Crystallographic Data Centre, CCDC687686). This data can be obtained free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/data request/cif.