Stille–Heck Coupling Sequences Applied in a Versatile New Access to Steroid Skeletons

HW Sünnemann, A Hofmeister, J Magull…

Index: Suennemann, Hans Wolf; Hofmeister, Anja; Magull, Joerg; De Meijere, Armin Chemistry - A European Journal, 2007 , vol. 13, # 13 p. 3739 - 3756

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Citation Number: 17

Abstract

Abstract A variety of enantiomerically pure steroidal compounds was synthesized utilizing a sequence of Stille and Heck cross-coupling reactions and subsequent thermal 6π- electrocyclizations. Highly chemoselective Stille couplings on the triflate moiety of several 2- bromocyclohex-1-enyl triflates with cis-and trans-fused bicyclo [4.3. 0] nonenylstannanes furnished the corresponding tricyclic bromobutadienes in good to excellent yields (70–97 ...