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Thermal and Photochemical Oxetane Formation. A Contribution to the Synthesis of Branched-Chain Aldonolactone

✍ Scribed by Jochen Mattay; Karl Buchkremer

Publisher: John Wiley and Sons
Year: 1988
Tongue: German
Weight: 455 KB
Volume: 71
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19880710506

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✦ Synopsis

Derivatives of 2-C-branched-chain erythrono-1 ,Clactones of the type 1 have been synthesized under reductive conditions using DIBAL from the oxetane 2, which is easily accessible from diethyl mesoxalate (4) and 2,2-diisopropyl-1,3-dioxole (3) in high yield by means of a catalytic cycloaddition. Similarly, 2 rearranges in presence of A1Me3 under formation of an erythronolactone with an additional branching at C(4). The corresponding oxetanes 7-9 from ethyl pyruvate (5) and ethyl trimethylpyruvate (6), respectively, have been studied with regard to their reductions yielding building blocks of branched-chain sugars.

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