Tetrahedron p. 10079 - 10088 (1998)
Update date:2022-07-31
Topics:
Wilmouth, Serge
Pellissier, Helene
Santelli, Maurice
Titanium tetrachloride mediated dialkylation of acetic anhydride, trifluoroacetic anhydride or difluorochloroacetic anhydride by 1,8- bis(trimethylsilyl)-2,6-octadiene (BISTRO) leads, respectively, to dl- 1- methyl-2,5-divinylcyclopentan-1-ol dl-1-difluoromethyl-2,5- divinylcyclopentan-1-ol or dl-1-trifluoromethyl-2,5-divinylcyclopentan-1-ol. Esterification of these compounds with 4-methoxybenzocyclobutene-l-carboxylic acid and then pyrolysis led to 3-methoxy-12-oxa-17-vinylestra-1,3,5(10)- trien-11-one and to corresponding 18,18-difluoro or 18,18,18-trifluoro derivatives. Further transformations give rise to 3-methoxy- 12-oxa-17-(2- oxoethyl)- 18.18-difluoroestra-1,3,5(10)-trien-11-one and to the corresponding 18,18,18-trifluoro derivative.
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