Camphorae: chiral intermediates fob the total synthesis of steroids

Stevens, Roger; Lawrence, David S.

doi:10.1016/s0040-4020(01)83472-4

Cited by 13 publications

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“…In addition, enantiopure derivatives of C(9)-substituted camphor 1(X/H) have also found application as chirality transfer agents, in this case, mainly as key chiral synthetic intermediates [e.g., 9-cyanocamphor 1(CN/H) in the elegant syntheses of vitamins B 12 and D developed by Stevens, or 9-bromocamphor 1(Br/H) in some total syntheses of furodisines, cannabidiols, and magnolols] (Figure ).…”

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Enantiospecific Access to Various C(9),C(10)-Disubstituted Camphors: Scope and Limitations

et al. 2004

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The valuable chiral sources C(9),C(10)-disubstituted camphors can be enantiospecifically obtained from the corresponding C(9)-substituted camphors by a general and straightforward synthetic method. This method involves the electrophilic treatment of a key 2-methylenenorbornan-1-ol intermediate, followed by a controlled tandem carbon-carbon double-bond addition-Wagner-Meerwein rearrangement of the norbornane framework. Discussion of the results presented suggests possible extensions and limitations of the methodology used. The feasibility of this method has been exemplified by the highly efficient enantiospecific preparation of several interesting C(9)-halogen-, C(10)-halogen, O-, S-, or Se-substituted camphors.

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confidence: 99%