Synlett 2019; 30(07): 753-764
DOI: 10.1055/s-0037-1610346
account
© Georg Thieme Verlag Stuttgart · New York

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

Yuebao Zhang
,
Ji Lu
,
Hongze Li
,
Xianwei Sun
,
Lu Gao
,
We are grateful for financial support from the NSFC (21622202, 21290180) and the MOST (2017ZX09101003-005-004).
Further Information

Publication History

Received: 08 November 2018

Accepted after revision: 08 November 2018

Publication Date:
18 December 2018 (online)


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