A Novel Intramolecular Heck Reaction: Synthesis of a Cholesterol ‐ Baccatin III Hybrid

John J. Masters, David Jung, Samuel J. Danishefsky, Lawrence B. Snyder, Tae Kyo Park, Richard C. A. Issacs, Cheryl A. Alaimo, Wendy B. Young

Angewandte Chemie International Edition in English · 1995 · 31 citations · 16 references

Concepts

Abstract

Despite strong repulsion between the methyl groups, the intramolecular Heck reaction of cyclohexenyl trifluoromethanesulfonate 1, available from 5-α-cholestan-3-one, proceeds in 50% yield. The product of the Heck reaction can be converted in a few subsequent steps into the cholesterol-baccatin III hybrid 2.

References

16