✦ LIBER ✦

Stereoselective synthesis of octahydro-3bH-[1,3]dioxolo[4″,5″:4′,5′]furo[2′,3′:5,6]pyrano[4,3-b]quinolines via intramolecular hetero-Diels–Alder reactions catalyzed by bismuth(III) chloride

✍ Scribed by Gowravaram Sabitha; E Venkata Reddy; J.S Yadav; K.V.S Rama Krishna; A Ravi Sankar

Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 156 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)00704-9

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✦ Synopsis

A new, efficient and stereoselective synthesis of furo[2%,3%:5,6]pyrano [4,3-b]quinoline derivatives 3 and 3% has been achieved by intramolecular hetero-Diels-Alder reactions of aldimines generated in situ from aromatic amines and the O-allyl derivative of the chiral sugar derived aldehyde 2 in acetonitrile in the presence of a catalytic amount of BiCl 3 . The products are formed with extremely high trans selectivity in good to excellent yields.

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