Tetrahedron

Novel Partial Synthetic Approaches to Replace Carbons 2, 3, 4 of Steroids. A Methodology to Label Testosterone and Progesterone with 13 C in the Steroid A Ring. …

K Kockert, FW Vierhapper

Index: Kockert, Karlheinz; Vierhapper, Friedrich W Tetrahedron, 2000 , vol. 56, # 51 p. 9967 - 9974

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Citation Number: 12

Abstract

Fragmentation of the A ring of the steroid hormone testosterone to yield the 10-formyl-5-oxo- des A intermediate was achieved by lactolization, lactonization, ozonolysis, and oxidation of the resulting methylol group. The reconstruction of the A ring was carried out via a Wittig synthesis with triphenylphosphoranylidene-2-propanone-13C3. Syntheses of the ylide, of the 13C3-testosterone, and of 13C3-progesterone took place in acceptable yields.