Studies in Steroid Total Synthesis. I. Resolution of a Bicyclic Intermediate
β Scribed by Speziale, A. John; Stephens, John A.; Thompson, Quentin E.
- Book ID
- 120477846
- Publisher
- American Chemical Society
- Year
- 1954
- Tongue
- English
- Weight
- 422 KB
- Volume
- 76
- Category
- Article
- ISSN
- 0002-7863
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π SIMILAR VOLUMES
Preparation of the "Ziegler key intermediate" 2from lactone 3, readily obtained from hydroxy-O-ionone, was studied. In a first exploratory approach, lactones 11 and 13 were obtained but further transformations aimed at setting the ring junction were unsuccessful due to unexpected rearrangements. Thr
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