@article{30c22d8fd0f6491da79d13a766e0e6f9,
title = "Steroids and related natural products-XVII. Conversion of lanosterol to 14α-methyl steroids",
abstract = "The possibility of abnormal steroid biosyntheses leading to in vivo formation of certain 14α-methyl steroids was discussed. In order to further evaluate this proposal, preparation of 14α-methyl steroids related to the androgenic hormones was undertaken. Initially, a thirteen-step degradation sequence was developed for converting isocholesterol (crude lanosterol) to 3-oxo-17β-hydroxy-4,4,14α-trimethyl-5α-androstane.",
author = "Pettit, {G. R.} and P. Hofer and Bowyer, {W. J.} and Kasturi, {T. R.} and Bansal, {R. C.} and Kadunce, {R. E.} and B. Green",
note = "Funding Information: {\textquoteleft} Refer to G. R. Pettit. A. K. Das Gupta and U. R. Ghatak, Steroids1,137 (1963). for the preceding contribution. 1 A summary of this study was presented (August 27. 1962) at The SecondI nternationaSl ymposium on the Chemislryo f Natural Products,P rague, Czechoslovakia. S This investigation was supported by PHS Research Grants CY-4074, CY-l074(Cl-C3), and CA 04074-05 from the National Cancer Institute, Public Health Service. {\textquoteright} For example, see: R. B. Clayton and K. Bloch,J. Eiol. Chem. 218,319 (1956) and F. Gautschi and K. Bloch, /bid. 233, 1343( 1958). {\textquoteright} Excellent discussions of cholesterol biosynthesis have been presented by: A. Wettstein, Experienriu 17, 329( 1961): W. Comforth, R. H. Cornforth. A. Pelter, M. G. Homing and G. Popjak, Terru-hedron5 , 31I (1959); P. Crabbe. Rec. Chem.P rogr. 20, 189 (1959); and J. W. Comforth, ./. Lipid Res. 1. 3 (1959). * Refer to A. Wettstein, ref. 5 for a valuable review of this subject and leading literature citations. {\textquoteright} The physiological activity displayed by I I-oxo-l4a-methyl-progesterone, o, W. Voser, H. Heusser, 0. Jeger and L. Ruzicka. Helu. Chim.A cfo 36,299( 1953)a, nd several related biogenetic considera-tions inspired a study leading to synthesis of 3~-hydroxy-2O-oxo-4,4,14a-trimethyl-5a-pregnane (Xa) by b. C. S. Barnes,A usfr.1. Chem. 9,228 (1956). Both l4a-methyl steroids were obtained by degradation of lanosterol.",
year = "1963",
doi = "10.1016/S0040-4020(01)98573-4",
language = "English (US)",
volume = "19",
pages = "1143--1152",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "7",
}