Total Synthesis of Bryostatin 8 and (–)-Exiguolide: Applications of an Organosilane Strategy

Dedication to Professor Yong-Qiang Tu on the occasion of his 60^th birthday

Abstract

In this Account, we give an overview of our recent efforts towards the total synthesis of two marine natural products: bryostatin 8 and (–)-exiguolide. The central theme is to highlight the power of the organosilane strategy, which was characterized with our geminal bis(silanes)-based methodologies for constructing the unique exocyclic enoate-substituted pyran rings.

1 Introduction

2 Background of Bryostatins and (–)-Exiguolide

3 Constructing the B-Ring of Bryostatins

4 Total Synthesis of (–)-Exiguolide via an Organosilane Strategy

5 Constructing the C-Ring of Bryostatins

6 Total Synthesis of Bryostatin 8

7 Conclusion

Key words

total synthesis - macrolides - organosilane - Prins cyclization - Brook rearrangement

• References and Notes


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