Structural Correction II: The Steroid Series

 

The Steroids structural correction Dr. Hekmat B Antaki (1923–1992)

Antaki reassigned the structure from the angular [2′:3′-3:4] to the linear [2′:3′-3:2] cholestane. The revised assignment corrected a structure co-authored by V. Petrow, Antaki's collaborator and co-author on the published paper.

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In Part II of his doctoral thesis (Queen Mary College, University of London, 1950, pp. 91–94), Antaki re-examined the indolo-cholestane that Dorée and Petrow had formulated as the angular isomer in 1935. The angular assignment had rested on surface-film measurements that were themselves inconclusive. Working from the established chemistry of the cholestanones, Antaki reassigned the structure from the angular [2′:3′-3:4] to the linear [2′:3′-3:2] cholestane. The revised assignment corrected a structure co-authored by V. Petrow, Antaki's collaborator and co-author on the published paper.

The full argument was set out in the thesis and published in compressed form in Part XII of the steroid work (J. Chem. Soc., 1951, 901). The reassignment was confirmed experimentally by Y. Ban and Y. Sato (Chem. Pharm. Bull., 1965, 13, 1073), who established the linear structure by ozonolytic degradation, carrying it through to the known Windaus–Uibrig acid. B. Robinson's review of the Fischer indole synthesis (Chem. Rev., 1969) records the same citation.

The steroid correction as written in the doctoral thesis, 1950, with the structural scheme showing the reassignment from the angular to the linear indolo-cholestane.