1. Synthesis of the Macrolactone Cores of Maltepolides via a Diene–Ene Ring-Closing Metathesis Strategy
- Author
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Lars Eric Bendel, Man Ki Sit, Hui Hui Cao, Wei-Min Dai, Wen Zhang, Tsz Chun Yip, and Yan-Dong Wu
- Subjects
chemistry.chemical_classification ,Double bond ,Diene ,Stereochemistry ,Organic Chemistry ,Epoxide ,Total synthesis ,Conjugated system ,Biochemistry ,chemistry.chemical_compound ,Ring-closing metathesis ,chemistry ,Biosynthesis ,Physical and Theoretical Chemistry ,Ene reaction - Abstract
Synthesis of the C19-truncated maltepolide E has been accomplished via a diene–ene RCM strategy without damage to the C11–C14 alkenyl epoxy unit. Upon release of the C17-OH group, it attacked at the C14 position with double bond migration and epoxide ring-opening to furnish the C19-truncated maltepolide A and B as proposed for the biosynthesis of maltepolides. Preliminary cytotoxicity data of the synthesized C19-truncated maltepolides against L929 mouse fibroblast cell line suggest irrelevance of the vinyl epoxide and importance of the conjugated dienyl keto unit for the observed anticancer activity.
- Published
- 2023
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