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Updated: Jun 19, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Stereoselective synthesis of the C31-C40/C43-C52 unit of amphidinol 3
Mitsunori Kanemoto1, Michio Murata, Tohru Oishi
1Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan.
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.
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The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.

