Concise Report
Modular Total Synthesis of (–)-Palmyrolide A and (+)-(5S,7S)-Palmyrolide A via Ring-Closing Metathesis and Alkene Isomerization†
Yecai Lai,
Wei-Min Dai,
Yecai Lai
Laboratory of Advanced Catalysis and Synthesis, Department of Chemistry and Hong Kong Branch of the Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou), The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, China
Current address: Baiyunshan Pharmaceutical General Factory, Guangzhou Baiyunshan Pharmaceutical Holdings Co., Ltd., Guangzhou 510515, China.
Search for more papers by this authorCorresponding Author
Wei-Min Dai
Laboratory of Advanced Catalysis and Synthesis, Department of Chemistry and Hong Kong Branch of the Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou), The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, China
E-mail: [email protected]Search for more papers by this authorYecai Lai,
Wei-Min Dai,
Yecai Lai
Laboratory of Advanced Catalysis and Synthesis, Department of Chemistry and Hong Kong Branch of the Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou), The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, China
Current address: Baiyunshan Pharmaceutical General Factory, Guangzhou Baiyunshan Pharmaceutical Holdings Co., Ltd., Guangzhou 510515, China.
Search for more papers by this authorCorresponding Author
Wei-Min Dai
Laboratory of Advanced Catalysis and Synthesis, Department of Chemistry and Hong Kong Branch of the Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou), The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, China
E-mail: [email protected]Search for more papers by this author†
Dedicated to the 70th anniversary of Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences.
Abstract
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.
Supporting Information
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Appendix S1: Supporting Information |
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