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The total synthesis of the water mold sex hormone oogoniol

โœ Scribed by Toshiaki Mase; Junji Ichita; Joseph P. Marino; Masato Koreeda

Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
256 KB
Volume
30
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

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) and CuCN to the steroidal 150,168-epoxy-17(20)(E)-ethylidene 2.

OH la R=H

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