Stereoselective synthesis of the C31-C40/C43-C52 unit of amphidinol 3.
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.
Kanemoto
Mitsunori
M
Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan.
Murata
Michio
M
Oishi
Tohru
T
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D000095722:Amphidinols
D000475:Alkenes; D011714:Pyrans; C438973:amphidinol 3; D000095722:Amphidinols