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Intramolecular diels-alder reaction with furan diene. A new synthesis of 11-keto steroids

โœ Scribed by Luc A Van Royen; Roelant Mijngheer; Pierre J De Clercq

Publisher
Elsevier Science
Year
1983
Tongue
French
Weight
255 KB
Volume
24
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

A novel D + BCD + ABCD route to ll-keto steroids is reported involving a high yield stereoselective intramolecular Diels-Alder reaction of furan-diene 5a in water as a key-step.

The dienophilic side chain is readily introduced starting from 2 via a sequence involving alkylation with ethyl 4-iodo-3-ethoxycrotonate, reduction and acid hydrolysis.

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โœ Luc A. Van Royen; Roelant Mijngheer; Pierre J. De Clercq ๐Ÿ“‚ Article ๐Ÿ“… 1982 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 238 KB

Depending on the reaction conditions the intramolecular Diels-Alder reaction of furan-diene 14 yields predominantly either one of two adducts 16a and 16b , which possess the necessary --functionality for eventual transformation into corticosteroids. The dienophile was intro-

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