Journal
TETRAHEDRON
Volume 73, Issue 29, Pages 4160-4171Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2016.11.004
Keywords
Cycloaddition; Oxidation; Alkaloids; Total synthesis; Natural products
Categories
Funding
- NSF [CHE-1262040, CHE-1564340]
- NIH NRSA Postdoctoral Fellowship [F32 GM103058]
- Direct For Mathematical & Physical Scien [1564340] Funding Source: National Science Foundation
- Division Of Chemistry [1564340] Funding Source: National Science Foundation
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1262040] Funding Source: National Science Foundation
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Driven by a new biogenetic hypothesis, the first total synthesis of alsmaphorazine B and several related indole alkaloids has been achieved. Numerous early approaches proved unsuccessful owing to unproductive side reactivity; nevertheless, they provided important clues that guided the evolution of our strategy. Critical to our success was a major improvement in our Zincke aldehyde cycloaddition strategy, which permitted the efficient gram-scale synthesis of akuammicine. The sequential chemoselective oxidations of akuammicine leading up to the key oxidative rearrangement also yielded several biogenetically related indole alkaloids en route to alsmaphorazine B. (C) 2016 Elsevier Ltd. All rights reserved.
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