Stereoselective Total Synthesis of (+)-Casuarine via a Functionalized Pyrrolidine

Abstract

The stereoselective total synthesis of (+)-casuarine has been achieved via a functionalized pyrrolidine obtained from a chiral 1,3-oxazine. The synthetic strategy includes a stereoselective dihydroxylation reaction using osmium tetroxide and stereoselective Grignard-type vinyl addition reaction as the key steps to generate the two new stereocenters. The dihydroxylation catalyzed by osmium tetroxide formed anti-amino alcohol, and the vinyl addition formed syn-alcohol. (+)-Casuarine was prepared from the functionalized pyrrolidine over 11 steps in an overall yield of 16%.

Key words

total synthesis - natural products - stereoselective synthesis - dihydroxylation - Grignard reaction - annulation - heterocycles

Publikationsverlauf

Eingereicht: 25. November 2021

Angenommen nach Revision: 20. Dezember 2021

Artikel online veröffentlicht:
14. Februar 2022

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