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Synthesis 2022; 54(10): 2473-2479
DOI: 10.1055/s-0041-1737844
DOI: 10.1055/s-0041-1737844
paper
Stereoselective Total Synthesis of (+)-Casuarine via a Functionalized Pyrrolidine
This work was supported by Yonsung Fine Chemicals Co., Ltd.
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 - heterocyclesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0041-1737844.
- Supporting Information
Publikationsverlauf
Eingereicht: 25. November 2021
Angenommen nach Revision: 20. Dezember 2021
Artikel online veröffentlicht:
14. Februar 2022
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For selective reports of stereoselective Upjohn dihydroxylations, see: