Biomimetic polyene cyclizations. Participation of the (trimethylsilyl) acetylenic group and the total synthesis of the D-homosteroid system

WS Johnson, TM Yarnell, RF Myers…

Index: Johnson, William S.; Yarnell, Thomas M.; Myers, Robert F.; Morton, Douglas R.; Boots, Sharon G. Journal of Organic Chemistry, 1980 , vol. 45, # 7 p. 1254 - 1259

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Citation Number: 24

Abstract

The aim of this study was to examine the (trimethylsily1) acetylenic group as a terminator in biomimetic polyene cyclizations. Two cyclization substrates, 2 and 4, containing this group were synthesized by the sequences outlined in Schemes I and 11. Cyclization of trienynol2 with trifluoroacetic acid in 1, 2-dichloroethane containing ethylene carbonate afforded a 19% yield of presumed ketone 18. Several difficulties such as the low yield in the cyclization ...