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Synthetic studies on the ceveratrum alkaloid skeleton

✍ Scribed by Keith Jones; Roger F. Newton; Christopher J. Yarnold

Book ID: 104207326
Publisher: Elsevier Science
Year: 1996
Tongue: French
Weight: 520 KB
Volume: 52
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(96)00074-9

No coin nor oath required. For personal study only.

✦ Synopsis

l-(2-Cyclohexenyl-l-carbonyl)-piperidine-2-carboxaldehyde oxime (23) was prepared in 5 steps from pyridine-2-carboxaldehyde. Oxidation with NaOCI afforded the corresponding nitrile oxide which cyclized to give a 1:1 ratio of diastereomers 2aot. 3,4.5,5a~9,10,11a~,llcct-decahydro-6H,8H-[1,2] benzisoxazolo [3,4-ab] quinolizin-6-one (24A) and 2act. 3,4,5,5a~9,10,1 laa, 11 co~-decahydro-6H,8H-[ 1,21 benzisoxazolo [3,4-ab] quinolizin-6-one (24B) in a best yield of 30%.

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