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Bicyclo[2.2.1]heptanes as intermediates in the synthesis of steroids. Total synthesis of estrone

โœ Scribed by Grieco, Paul A.; Takigawa, Tetsuo; Schillinger, William J.

Book ID
121423606
Publisher
American Chemical Society
Year
1980
Tongue
English
Weight
626 KB
Volume
45
Category
Article
ISSN
0022-3263

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Bicyclo[2.2.1]heptanes as intermediates
Bicyclo[2.2.1]heptanes as intermediates in the synthesis of steroids. Total synthesis of estrone
โœ Grieco, Paul A.; Takigawa, Tetsuo; Schillinger, William J. ๐Ÿ“‚ Article ๐Ÿ“… 1980 ๐Ÿ› American Chemical Society ๐ŸŒ English โš– 626 KB

A synthesis of dl-estrone has been accomplished by employing the key bicyclo[2.2.l]heptene intermediate 2 prepared from ketal ester 16 via a series of reactions featuring the remarkable stereospecific alkylation of 16 with 2-(4-methoxybenzocyclobutenyl)ethyl iodide. Intermediate 2 provided direct ac