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Synthesis of chiral pyranocyclohexane, oxepanocyclohexane, and furylpyran and -oxepane systems by the application of intramolecular nitrone and nitrile oxide cycloaddition of carbohydrate derivatives

✍ Scribed by Arani Pal; Ashoke Bhattacharjee; Anup Bhattacharjya; Amarendra Patra

Book ID: 104209283
Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 722 KB
Volume: 55
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(99)00105-2

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✦ Synopsis

Chiral nonracemic pyranocyclohexanes 7 and 8 and oxepanocyclohexane It and 12 were obtained from a single 1,2-isopropylidene-3-O-cyclohexenyl carbohydrate aldehyde 4 via intramolecular nitrile oxide cycloaddition, and were converted to 2-(2'-tetrahydrofuryl)pyran 28, which incorporates the lasalocid skeleton, and the related oxepane derivative 32 respectively, through modification of the furanoside ring by. applying 2-O-allyl carbohydrate nitrone cycloaddition.

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