Stereoselective synthesis of the C31-C40/C43-C52 unit of amphidinol 3.

Abstract

A concise synthesis of a tetrahydropyran ring system corresponding to the C31-C40 and C43-C52 units of amphidinol 3 is described. Successive chemoselective reactions, i.e., cross-metathesis to differentiate the iodoolefin from the terminal olefin and Sharpless asymmetric dihydroxylation on the resulting E-olefin, resulted in expeditious synthesis of an intermediate that was then cross-coupled to afford an E,E-diene system. Four contiguous stereogenic centers were installed via construction of the tetrahydropyran ring by means of Katsuki-Sharpless asymmetric epoxidation, 6-endo-tet cyclization, and Sharpless asymmetric dihydroxylation.

DOI: 10.1021/jo901793f

Cite this paper

@article{Kanemoto2009StereoselectiveSO, title={Stereoselective synthesis of the C31-C40/C43-C52 unit of amphidinol 3.}, author={Mitsunori Kanemoto and Michio Murata and Tohru Oishi}, journal={The Journal of organic chemistry}, year={2009}, volume={74 22}, pages={8810-3} }