Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 128, Issue 40, Pages 13255-13260Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja063860+
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Funding
- NIGMS NIH HHS [GM67659, R01 GM067659-06A1, R01 GM067659] Funding Source: Medline
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A diastereoselective [4 + 2]-annulation of vinyl carbodiimides with chiral N-alkyl imines has been developed to access the stereochemically rich polycyclic guanidine cores of the batzelladine alkaloids. Application of this strategy, together with additional key steps such as long-range directed hydrogenation and diastereoselective intramolecular iodo-amination, led to highly convergent total syntheses of (-)-batzelladine D and (+)- batzelladine A with excellent stereocontrol.
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