Cobalt-catalyzed one-step assembly of B-ring aromatic steroids from acyclic precursors
Because of their varied physiological activity, steroids are important testing grounds on which to explore the utility of novel synthetic methodology. In this study cobalt, in the form of CpCo(CO)/sub 2/ is used as a matrix around which to assemble natural and unnatural polycyclic products, including the steroid nucleus. In this way, the total synthesis of A-ring aromatic systems of the estrone type was achieved via the D ..-->.. ABCD and A ..-->.. ABCD strategies. An approach is reported here in which all four rings are assembled (0 ..-->.. ABCD) in one step to give B-ring aromatic derivatives with complete control of the crucial stereochemistry of the C,D-ring juncture. This strategy has been accomplished previously only by employing biomimetic cyclizations and not en route to the rate target class of compounds which has never been constructed by total synthesis. 13 references, 1 table.
- Research Organization:
- Univ. of California, Berkeley
- OSTI ID:
- 6909421
- Journal Information:
- J. Am. Chem. Soc.; (United States), Vol. 108:4
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
COBALT
CATALYTIC EFFECTS
ESTRONE
CHEMICAL PREPARATION
CATALYSIS
CATALYSTS
COBALT COMPOUNDS
EXPERIMENTAL DATA
STEREOCHEMISTRY
DATA
ELEMENTS
ESTRANES
ESTROGENS
HORMONES
HYDROXY COMPOUNDS
INFORMATION
KETONES
METALS
NUMERICAL DATA
ORGANIC COMPOUNDS
STEROID HORMONES
STEROIDS
SYNTHESIS
TRANSITION ELEMENT COMPOUNDS
TRANSITION ELEMENTS
400201* - Chemical & Physicochemical Properties