Tandem Wessely oxidation and intramolecular Diels–Alder reactions. III. Synthesis of isotwistanes
作者:
Peter Yates,
Tadas S. Macas,
期刊:
Canadian Journal of Chemistry
(NRC Available online 1988)
卷期:
Volume 66,
issue 1
页码: 1-10
ISSN:0008-4042
年代: 1988
DOI:10.1139/v88-001
出版商: NRC Research Press
数据来源: NRC
摘要:
Wessely oxidation ofo-(3-alkenyl) phenols (5) with lead tetraacetate gives 6-acetoxy-6-(3-alkenyl)-2,4-cyclohexadien-1-ones (6), which undergo intramolecular Diels–Alder reactions to give isotwistene (hexahydro-1,5-methanoindene) derivatives (7). These, on hydrolysis followed by oxidation with periodic acid, give hexahydro-1-oxo-1H-indene-5-carboxylic acids (41,46). Compounds5were prepared either by Grignard coupling ofo-methoxybenzyl chloride with allyl halides followed by de-O-methylation with sodium thioethoxide or via reduction of dihydrocoumarins(18–20)to 2-chromanols(21–23)with diisobutylaluminum hydride, followed by Wittig reaction of these with ethyl (triphenylphosphoranylidene)acetate.
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