C-6 Hydroxylated Steroids. IV.<sup>1</sup> 6-Hydroxylated 17α-Acetoxyprogesterone, 17α-Acetoxy-6-methylprogesterone, and Related Compounds

Dusza, John P.; Joseph, J. P.; Bernstein, Seymour

doi:10.1021/jo01036a021

Cited by 13 publications

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“…Epoxidation of (-)-Thujopsene (1).-The isomerization of epoxides to ketones with boron trifluoride etherate involves a stereospecific hydride shift. [22][23][24] Epoxidation, like hydroboration, appears also to involve an exothermic process proceeding through a cyclic transition state25,26 with large steric requirements. Hence it would also be expected to take place on thujopsene from the ß side to give a ß-epoxide (6).…”

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Hydroboration of terpenes. VIII. Hydroboraction of (-)-thujopsene. Configurations of the isomeric 3-thujopsanols and 3-thujopsanones

Acharya¹,

Brown²

1970

J. Org. Chem.

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Conformational analysis suggests that thujopsene (1) can exist in two possible conformations, steroidal I and nonsteroidal II. In the steroidal conformation, the side (a) away from the cyclopropane ring should be relatively inaccessible to reactions sensitive to steric requirements, whereas, in the nonsteroidal conformation, it is the side (ß) toward the cyclopropane ring that should be relatively inaccessible. Hydroboration of (-)-thujopsene takes place exclusively from the ß side, as indicated by the isolation of a single alcohol (+ )-3-thujopsanol (2). The structure of (+ )-3-thujopsanol has been established by determining the absolute configuration of the alcohol

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confidence: 99%