Abstract
Abstract A marine polyether natural product okadaic acid is known to be a potent and specific inhibitor of protein phosphatases 1 and 2A. Herein, concise synthesis of the C15-C38 fragment of okadaic acid is reported. We investigated two different strategies for the construction of two spiroacetal substructures found in the target compound. The first strategy involved Suzuki-Miyaura coupling for the synthesis of endocyclic enol ethers and subsequent spiroacetalization. The second strategy exploited Suzuki-Miyaura coupling for the synthesis of exo-olefins as the precursor of spiroacetals. An alkynylaluminum-anomeric sulfone coupling effectively assembled the key spiroacetal substructures and completed the target compound.
Original language | English |
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Article number | 26603 |
Pages (from-to) | 6369-6383 |
Number of pages | 15 |
Journal | Tetrahedron |
Volume | 71 |
Issue number | 37 |
DOIs | |
Publication status | Published - 2015 Aug 7 |
Keywords
- Anomeric sulfones
- Marine toxins
- Polyethers
- Spiroacetals
- Suzuki-Miyaura coupling
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry