Synthesis of Key Fragments of 19-Membered Cytotoxic Macrolide Amphidinolide E

Author(s): Seetaram Mohapatra , Sabita Nayak , Sambita K. Mishra , Priyabrata Pattanaik .

Journal Name: Letters in Organic Chemistry

Volume 10 , Issue 1 , 2013

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Amphidinolide E is a 19-membered macrolide possessing potent cytoxic activity. The macrolide core having two key intermediates alcohol and acid was synthesized efficiently. The THF ring segment was synthesized from Dglucose as chiral precursor, whereas the cis-tetrahydrofuran ring was established by stereoselective intramolecular oxymercuration reaction. The acid component having E-diene was established by Stille cross coupling of vinyl iodo and vinly stannane segment. Coupling reaction of acid segment and alcohol was examined.

Keywords: Amphidinolide, Bestmann reagent, natural product, oxymercuration, stereoselectivity, stille coupling, Takai olefination, biological, intermediates, Debenzylation

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Article Details

Year: 2013
Page: [65 - 69]
Pages: 5
DOI: 10.2174/1570178611310010015

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PDF: 49