Transannular cyclization of 5β-cholestan-2α-ol leading to 2α,9α-epoxy-5β-cholestane

✍ Scribed by Munemitsu Tomoeda; Toshitaka Koga

• Book ID: 104240486
• Publisher: Elsevier Science
• Year: 1965
• Tongue: French
• Weight: 359 KB
• Volume: 6
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)89218-2

✦ Synopsis

In connection uith the general objective of introducing a functional group into an inactivated carbon atom in the steroid nucleue, a number'of papere (1.2) have recently appeared which showed that varioue steroidal alcohols could react with lead tetraacetate in non-polar eolvents forming tetrahydrofuran and tetrahydropyran derivatives, cyclization occuring, for instance, in the following directione: lla+la, 2fk19, 3a+9a**, 4u+9a**, 4@+19, 68+19, 11-8 and +l9, and 2-18. To our lrnowledge, however, no paper has dealt with the cyclization from 2a to 9a po-BitiOnS, although inspection of a Dreiding BtereOmOdel (I) of l All new compounde eyntheeized gave correct analyeea.