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Synlett 2019; 30(07): 753-764
DOI: 10.1055/s-0037-1610346
DOI: 10.1055/s-0037-1610346
account
Total Synthesis of Bryostatin 8 and (–)-Exiguolide: Applications of an Organosilane Strategy
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
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References and Notes
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For selective reviews on organosilanes, see:
Brook rearrangement – for selected examples, see:
Danheiser cyclopentene annulation:
Fleming–Tamao oxidation:
Hiyama-Denmark Cross coupling:
Mukaiyama aldol:
Peterson olefination:
Sakurai allylation:
Smith–Tietze multicomponent dithiane linpinch coupling:
Silicon-tethered strategy:
For latest progresses achieved in our group, see:
For reviews on the bryostatins, see:
For the latest studies on bryostatin analogues, see:
For total synthesis of the bryostatins, see for bryostatin 7:
Bryostatin 2:
Bryostatin 3:
Formal synthesis of bryostatin 7:
Bryostatin 16:
Bryostatin 1:
Bryostatin 9:
Bryostatin 7:
Bryostatin 1:
For total synthesis, see:
For selected reviews, see:
For the latest reviews on RCM reactions, see:
For selected reviews, see:
For selected works, see:
For selected reviews on the Brook rearrangement, see:
For a review on Fleming–Tamao oxidation, see: