Abstract
The first total synthesis of gambierol, a marine polycyclic ether toxin, has been achieved. Highly efficient synthesis of the ABC and EFGH ring fragments allowed us to prepare those two advanced intermediates in multi-gram quantities. The key feature of the present total synthesis is the B-alkyl Suzuki-Miyaura coupling tactics, which culminated in the union of the advanced intermediates and convergent synthesis of the octacyclic polyether core. Introduction of the sensitive triene side chain via Pd(PPh3) 4/CuCl/LiCl-promoted Stille coupling was conducted at the final step of the synthesis. The present total synthesis supplied useful quantities of gambierol and its structural analogues for detailed biological studies: an interesting observation was gained through pathological studies. Also, preliminary structure-activity relationship studies revealed that the functionalities present in the H ring and unsaturated side chain are crucial for notent toxicitv asainst mice.
Original language | English |
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Pages (from-to) | 742-751 |
Number of pages | 10 |
Journal | Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry |
Volume | 61 |
Issue number | 8 |
DOIs | |
Publication status | Published - 2003 Aug |
Keywords
- B-alkyl Suzuki-Miyaura coupling
- Ciguatera
- Ciguatoxin
- Gambierol
- Marine toxin
- Pathological studies
- Polycyclic ethers
- Stille reaction
- Structure-activity relationship
- Total synthesis
ASJC Scopus subject areas
- Organic Chemistry