ArticleTetrahedron2017
A Sequential Cycloaddition Strategy for the Synthesis of Alsmaphorazine B Traces a Path Through a Family of
Article in Tetrahedron, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed, 31 citations in OpenAlex.
- Collective asymmetric synthesis of the Strychnos alkaloids via thiophene S,S-dioxide cycloadditions.Nature chemistry · 2026Article
- Preparation of spirocyclic oxindoles by cyclisation of an oxime to a nitrone and dipolar cycloaddition.Beilstein journal of organic chemistry · 2025Article
- A Synthesis of Alstonlarsine A via Alstolucines B and F Demonstrates the Chemical Feasibility of a Proposed Biogenesis.Angewandte Chemie (International ed. in English) · 2023Article
- Total Synthesis of (-)-Voacinol and (-)-Voacandimine C.Journal of the American Chemical Society · 2022Article
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
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
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