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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
P ARANI, A BHATTACHARJEE, A BHATTACHARJYA, A PATRA
Published in PERGAMON-ELSEVIER SCIENCE LTD
1999
Volume: 55
   
Issue: 13
Pages: 4123 - 4132
Abstract
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.
About the journal
JournalData powered by TypesetTetrahedron
PublisherData powered by TypesetPERGAMON-ELSEVIER SCIENCE LTD
ISSN0040-4020