Synthesis of Principal Building Blocks of Amphidinolides of the G and H Families

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Abstract

Based on the reactions of diastereoselective allylation of (R)-2,3-O-cyclohexylideneglyceraldehyde with methyl 3-(bromomethyl)but-3-enoate and its allylstannyl derivative, unsaturated lactones (6R)- and (6S)-6-[(2R)-1,4-dioxaspiro[4.5]dec-2-yl]-4-methyl-5,6-dihydro-2H-pyran-2-ones were synthesized. After highly diastereoselective reduction, these lactones found application in the implementation of a new retrosynthetic scheme for the preparation of С5–С14, С15–С19 and С20–С26 building blocks of amphidinolides of the G and H families.

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About the authors

Irina V. Mineeva

Institute for Physical Chemical Problems of the Belarusian State University

Author for correspondence.
Email: i.mineyeva@yandex.ru
ORCID iD: 0000-0002-6422-1967
Belarus, 14, Leningradskaya St., Minsk, 220006

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