Asymmetric Synthesis of (−)-Swainsonine

We report a new asymmetric synthetic method for (−)-swainsonine utilizing a chiral oxazoline precursor. The key features in this strategy are the diastereoselective oxazoline formation reaction catalyzed by palladium(0), diasteroselective dihydroxylation, and the stereocontrolled allylation reaction...

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Bibliographic Details
Published in:Journal of organic chemistry 2009-05, Vol.74 (10), p.3962-3965
Main Authors: Tian, Yong-Shou, Joo, Jae-Eun, Kong, Bae-Soo, Pham, Van-Thoai, Lee, Kee-Young, Ham, Won-Hun
Format: Article
Language:English
Subjects:
Antineoplastic Agents, Phytogenic - chemical synthesis
Antineoplastic Agents, Phytogenic - chemistry
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Oxazoles - chemistry
Preparations and properties
Stereoisomerism
Substrate Specificity
Swainsonine - chemical synthesis
Swainsonine - chemistry
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Summary:We report a new asymmetric synthetic method for (−)-swainsonine utilizing a chiral oxazoline precursor. The key features in this strategy are the diastereoselective oxazoline formation reaction catalyzed by palladium(0), diasteroselective dihydroxylation, and the stereocontrolled allylation reaction with TiCl4.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo802800d