Process for synthesis of steroidal allylic tert. alcohols

Details Process for synthesis of steroidal allylic tert. alcohols Process for synthesis of steroidal allylic tert. alcohols

1994-02-14

1995-09-12

Richter, Johann

Organic compounds -- part of the class 532-570 series

Organic compounds

Cyclopentanohydrophenanthrene ring system containing

552531, 552532, 552533, 552534, 552603, 540 95, 540 96, 540 97, 540108, 540109, 540112, C07J 7500

Patent

active

054497957

ABSTRACT:
A method for the preparation of a steroidal allylic tertiary alcohol is disclosed which involves the deprotonation of a sulfoxide with a strong base which is capable of deprotonating the methine proton which is .alpha. to the sulfoxide, in an inert solvent to give the anion; reaction of the anion with a steroidal spiro-2'-oxirane to give a steroidal .gamma.-hydroxysulfoxide; and thermolysis in the presence of a base other than calcium carbonate to give the steroidal allylic tertiary alcohol.

REFERENCES:
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patent: 5232917 (1993-08-01), Bolger et al.
Corey and Chaykovsky, "Dimethyloxosulfonium Methylide ((CH.sub.3).sub.2 SOCH.sub.2) and Dimethylsulfonium Methylide ((CH.sub.3).sub.2 SCH.sub.2). Formation and Application to Organic Synthesis", J. Am. Chem. Soc. 87 (6):1353-1364 (1965).
Guittet, E. and Julia, S., "A Simple Synthesis of 3,7-dimethylocta-1,5(E),7-trien-3-ol (E-Hotrienol)", Synth. Comm. 9 (4):317-323 (1979).
Okamura et al., "1-Arylsulfinyl-1-alken-1-yllithium", Chem. Lett.:517-520 (1978).
Sharma et al., "Synthesis of sultines via tert-butyl hydroxyalkyl sulfoxides", Can. J. Chem. 54:3012-3025 (1976).
Takano et al., "A Facile Synthesis of (R)-1-Benzyloxy-3-buten-2-ol", Synthesis (August):610-611 (1988).
Trost et al., "New Synthetic Reactions. Sulfenylations and Dehydrosufenylations of Esters and Ketones", J. Am. Chem. Soc. 98(16):4887-4902 (1976).

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