Modular Total Synthesis of (–)‐Palmyrolide A and (+)‐(5S,7S)‐Palmyrolide A via Ring‐Closing Metathesis and Alkene Isomerization

A pentamodule assembly approach has been established for total synthesis of the naturally occurring (–)‐palmyrolide A and (+)‐5,7‐epi‐palmyrolide A. By using the racemic tert‐butyl carbinol‐containing alkyl iodide, the two diastereoisomeric macrolides could be obtained from the same sequence of reac...

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Bibliographic Details
Published in:Chinese journal of chemistry 2021-01, Vol.39 (1), p.69-74
Main Authors: Lai, Yecai, Dai, Wei‐Min
Format: Article
Language:English
Subjects:
Alkene
Assembly
B‐Alkyl Suzuki–Miyaura cross‐coupling
Cross‐coupling
Iodides
Isomerization
Metathesis
Modular total synthesis
Ring‐closing metathesis
Synthesis
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Summary:A pentamodule assembly approach has been established for total synthesis of the naturally occurring (–)‐palmyrolide A and (+)‐5,7‐epi‐palmyrolide A. By using the racemic tert‐butyl carbinol‐containing alkyl iodide, the two diastereoisomeric macrolides could be obtained from the same sequence of reactions, demonstrating the flexibility of the multimodule assembly strategy for diverted total synthesis. The skeleton of (–)‐palmyrolide A is disassembled into five structural modules, each of which possesses two orthogonal functional groups and is ready for modular assembling reactions. Four of the five modules are commercial reagents, enabling concise synthesis of the target molecule.
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.202000458