Total synthesis of brevetoxin B.


The convergent total synthesis of brevetoxin B (1) has been achieved. The intramolecular allylation of the O,S-acetal 20, prepared from the alpha-chlorosulfide 17 and the alcohol 5, was carried out using AgOTf as a Lewis acid to give the diene 21, predominantly. Ring-closing metathesis of 21 with the Grubbs catalyst 23 afforded the hexacyclic ether 25 which was converted to the A-G ring segment 2 through several steps. The intramolecular allylation of the alpha-acetoxy ether 42, prepared from 2 and the J-K ring segment 3, followed by ring-closing metathesis provided the polycyclic ether framework 44. A series of reactions of 44, including oxidation of the A ring, deprotection of the silyl ethers, and selective oxidation of the resulting allylic alcohol, furnished 1.

Cite this paper

@article{Kadota2005TotalSO, title={Total synthesis of brevetoxin B.}, author={Isao Kadota and Hiroyoshi Takamura and Hiroki Nishii and Yoshinori Yamamoto}, journal={Journal of the American Chemical Society}, year={2005}, volume={127 25}, pages={9246-50} }