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

Chiral nonracemic pyranocyclohexanes 7 and 8 and oxepanocyclohexane 11 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 lasaloci...

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Bibliographic Details
Published in:Tetrahedron 1999-03, Vol.55 (13), p.4123-4132
Main Authors: Pal, Arani, Bhattacharjee, Ashoke, Bhattacharjya, Anup, Patra, Amarendra
Format: Article
Language:English
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Summary:Chiral nonracemic pyranocyclohexanes 7 and 8 and oxepanocyclohexane 11 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. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(99)00105-2