Journal
TETRAHEDRON
Volume 74, Issue 26, Pages 3188-3197Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2018.04.050
Keywords
Total synthesis; Alkaloid; Tropane; Batzelladine; Dehydrobatzelladine
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Funding
- National Institutes of Health (Chemistry Biology Interface Training Program) [T32GM067543]
- National Institutes of Health (NRSA fellowship) [F32GM110898-01A1]
- National Science Foundation [GRFP DGE-1752134]
- Yale University
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We recently reported a convergent strategy to access the polycyclic guanidinium alkaloid (+)-batzelladine B via an aldol addition retro-aldol aza-Michael addition cascade. Here we describe the application of this approach toward the total syntheses of (+)-batzelladine E, (-)-dehydrobatzelladine C, and (+)-batzelladine K. The identification of suitable methods to functionalize a common tropane core by electrophilic alkynylation and nucleophilic 1,2-addition were essential to generalizing this approach. We provide evidence for the intermediacy of an acylallene species in the cascade reaction. (C) 2018 Published by Elsevier Ltd.
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