Abstract
The polycyclic ether class of marine natural products presents formidable and challenging synthetic targets due to their structural complexity and exceptionally potent biological activities. We have developed a highly convergent strategy for the assembly of a huge polycyclic ether array, which features Suzuki-Miyaura cross-coupling of alkylboranes, generated from exocyclic enol ethers, with cyclic ketene acetal triflates or phosphates combined with reductive ring-closure. The utility of this strategy was demonstrated by its application to synthetic studies on ciguatoxins, and the total syntheses of gambierol and gymnocin-A.
1 Introduction
2 B-Alkyl Suzuki-Miyaura Coupling Strategy for Polycyclic Ether Synthesis
2.1 Suzuki-Miyaura Reaction of Ketene Acetal Triflates
2.2 Suzuki-Miyaura Coupling of Ketene Acetal Phosphates
3 Synthetic Studies toward Ciguatoxins
3.1 Synthesis of the ABCD Ring Fragment
3.2 Convergent Synthesis of the FGHIJKLM Ring Fragment
4 Total Synthesis of Gambierol
4.1 Synthesis Planning
4.2 Synthesis of the ABC Ring Fragment
4.3 First Generation Synthesis of the EFGH Ring Fragment
4.4 Second Generation Synthesis of the EFGH Ring Fragment
4.5 Synthesis of the Octacyclic Polyether Core
4.6 Completion of Total Synthesis of Gambierol
4.7 Biological Evaluation
5 Total Synthesis of Gymnocin-A
5.1 Retrosynthetic Analysis
5.2 Synthesis of the ABCD Ring Fragment
5.3 Synthesis of the FGHIJKLMN Ring Fragment
5.4 Completion of Total Synthesis of Gymnocin-A
6 Conclusion
Key words
cross-coupling - natural products - polycyclic ethers - Suzuki-Miyaura reaction - total synthesis
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