DEDICATED TO PROFESSOR HC BROWN ON HIS ... - Sigma-Aldrich

6.2. HMG-CoA Reductase
Inhibitor Analogs
The discovery of compactin and
mevinolin (Figure 7) two decades ago as
inhibitors of hydroxymethylglutaryl coenzyme
A reductase revolutionized research aimed at
the treatment of hypercholesterolemia. 70
Systematic studies of the analogs of
mevinolin have revealed that the key
pharmacophore necessary for drug action
is the β-hydroxy-δ-lactone unit. 71 Our
32 VOL. 35, NO. 1 • 2002
Figure 6. Chiral Dialkylallylboranes.
Scheme 20. Application of Allylboration. Synthesis of Epothilone A.
Scheme 21. Application of Allylboration. Synthesis of Nystatin A1.
synthesis of mevinolin analogs is shown in
Scheme 28. 72
7. Conclusion and Prospects
The borane continent that Professor
Brown discovered is truly vast. Allylboration
is only a small part of organoborane
chemistry. This review has covered only a
subsection of the still-developing area of
asymmetric “allyl”boration. We are currently
developing a variety of new “allyl”borating
agents, and investigating substrates other
than aldehydes.
8. Acknowledgments
Financial support from the Herbert C.
Brown Center for Borane Research 73 and
Aldrich Chemical Company is gratefully
acknowledged. Thanks are also due to the
dedicated members of my research group,
particularly Dr. M. Venkat Ram Reddy.