ArticleOrganic letters2012
A macrocyclic β-iodoallenolate intermediate is key: synthesis of the ABD core of phomactin A.
Article in Organic letters, 2012. 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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4 citing papers in PubMed.
- Unconventional Macrocyclizations in Natural Product Synthesis.ACS central science · 2020Review
- C-C Bond Cleavage Approach to Complex Terpenoids: Development of a Unified Total Synthesis of the Phomactins.Journal of the American Chemical Society · 2020Article
- Cascade cyclizations of acyclic and macrocyclic alkynones: studies toward the synthesis of phomactin A.The Journal of organic chemistry · 2013Article
- Gold (III) Chloride-Catalyzed 6-Advanced synthesis & catalysis · 2013Article
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3 authors.
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Abstract
An enantioselective strategy for the synthesis of phomactin natural products is described. The Lewis acid triggered cyclization of a β-iodoallenolate embedded in a 12-membered macrocycle was used to obtain a highly functionalized bicyclo[9.3.1]pentadecane in good yield and high diastereoselectivity. This iodoenone contains the substituents of the AD ring system of the phomactin family of natural products, appropriate for further functionalization. Synthesis of the oxadecalin core of phomactin A from the AD iodoenone intermediate was achieved. In this unusual strategy, rings A and B are both fashioned within a macrocyclic precursor.
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