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Synthesis 2019; 51(18): 3471-3476
DOI: 10.1055/s-0037-1611566
DOI: 10.1055/s-0037-1611566
paper
Total Syntheses of (–)-7-epi-Alexine and (+)-Alexine Using Stereoselective Allylation
This work was supported by Yonsung Fine Chemicals Co., Ltd.Weitere Informationen
Publikationsverlauf
Received: 11. April 2019
Accepted after revision: 09. Mai 2019
Publikationsdatum:
12. Juni 2019 (online)
Abstract
Total syntheses of (–)-7-epi-alexine and (+)-alexine were achieved by using stereoselective allylation via a functionalized pyrrolidine obtained from an extended chiral 1,3-oxazine. The synthetic strategies include pyrrolidine formation via oxazine cleavage and diastereoselective allylations of a pyrrolidine aldehyde. (–)-7-epi-Alexine and (+)-alexine were synthesized from anti,syn,anti-oxazine in 12 steps.
Key words
allylation - alkaloids - amino alcohols - diastereoselectivity - asymmetric synthesis - cyclizationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611566.
- Supporting Information
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