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- W3203092823 abstract "Chemical transformations that rapidly and efficiently construct a high level of molecular complexity in a single step are perhaps the most valuable in total synthesis. Among such transformations is the transition metal catalyzed [2 + 2 + 2] cycloisomerization reaction, which forges three new C-C bonds and one or more rings in a single synthetic operation. We report here a strategy that leverages this transformation to open de novo access to the Veratrum family of alkaloids. The highly convergent approach described herein includes (i) the enantioselective synthesis of a diyne fragment containing the steroidal A/B rings, (ii) the asymmetric synthesis of a propargyl-substituted piperidinone (F ring) unit, (iii) the high-yielding union of the above fragments, and (iv) the intramolecular [2 + 2 + 2] cycloisomerization reaction of the resulting carbon framework to construct in a single step the remaining three rings (C/D/E) of the hexacyclic cevanine skeleton. Efficient late-stage maneuvers culminated in the first total synthesis of heilonine (1), achieved in 21 steps starting from ethyl vinyl ketone." @default.
- W3203092823 created "2021-10-11" @default.
- W3203092823 creator A5003855700 @default.
- W3203092823 creator A5084550043 @default.
- W3203092823 date "2021-09-29" @default.
- W3203092823 modified "2023-10-10" @default.
- W3203092823 title "Enantioselective Total Synthesis of (+)-Heilonine" @default.
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- W3203092823 doi "https://doi.org/10.1021/jacs.1c08756" @default.
- W3203092823 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/8517970" @default.
- W3203092823 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/34585920" @default.
- W3203092823 hasPublicationYear "2021" @default.
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