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

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

Volume: 10 Issue: 1

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

Affiliation:

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

Abstract: 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.

Cite this article as:

Mohapatra Seetaram, Nayak Sabita, K. Mishra Sambita and Pattanaik Priyabrata, Synthesis of Key Fragments of 19-Membered Cytotoxic Macrolide Amphidinolide E, Letters in Organic Chemistry 2013; 10 (1) . https://dx.doi.org/10.2174/1570178611310010015