Application of intramolecular Heck reactions to the preparation of steroid and terpene intermediates having cis A-B ring fusions - model studies for the total synthesis of complex cardenolides

Sabine Laschat, Frank Narjes & Larry E. Overmann
The cis-fused tricyclic dienone 13 is the major product formed from intramolecular Heck cyclization of the dienyl triflate 12 (Scheme I). Similarly, the cis-hexahydrophenanthridine 22 is formed in good yield from Heck cyclization of the aryl triflate 21. This latter conversion demonstrates that allylic ether substitution is compatible with intramolecular Heck chemistry and suggests applications of this chemistry in the synthesis of highly oxidized cardenolides.
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