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Electrophile-mediated cyclizations of 6-O-benzyl-1,2-di- deoxy-3,4-O-isopropylidene-d-ribo-hex-1-enitol to derivatives of 2,5-anhydro-6-O-benzyl-3,4-O-isopropylidene-d-altro-hexitol

✍ Scribed by Fillmore Freeman; Kirk D. Robarge

Publisher: Elsevier Science
Year: 1985
Tongue: English
Weight: 633 KB
Volume: 137
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(85)85151-x

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✦ Synopsis

Electrophile

(bromine, iodine, mercuric acetate, mercuric trifluoroacetate, phenylselenyl chloride)-mediated cyclization of 6-0-benzyl-1,2-dideoxy-3,4-0isopropylidene-D-ribo-hex-l-enitol

(2) led exclusively to l-substituted derivatives of 2,5-anhydro-6-0-benzyl-3,4-O-isopropylidene-D-altro-hexitol

(3). The synthesis of alkene 2, together with mechanistic and stereochemical aspects of its cyclization to derivatives of hexitol 3 are discussed.

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