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The Total Synthesis of a Stereoisomer of the Sex Hormone Estrone 1

โœ Scribed by Bachmann, W. E.; Kushner, S.; Stevenson, A. C.


Book ID
120585955
Publisher
American Chemical Society
Year
1942
Tongue
English
Weight
928 KB
Volume
64
Category
Article
ISSN
0002-7863

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The water mold sex hormone oogoniol (la) has been synthesized from adrenosterone in 18 steps in 7.0% overall yield. The crucial step introduces the stereochemistry at C-15 and C-20 through a highly efficient 1,4-addition of the organocyanocuprate generated from the side chain Grignard reagent (fi) a