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Biomimetic Syntheses of Callistrilones A-E via an Oxidative [3 + 2] Cycloaddition.

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Concise total syntheses of callistrilones A-E have been achieved from 7 and commercially available α-phellandrene (8). The synthetic strategy, which was primarily inspired by the biogenetic hypothesis, was enabled by… Click to show full abstract

Concise total syntheses of callistrilones A-E have been achieved from 7 and commercially available α-phellandrene (8). The synthetic strategy, which was primarily inspired by the biogenetic hypothesis, was enabled by an oxidative [3 + 2] cycloaddition followed by a Michael addition and an intramolecular nucleophilic addition to construct the target molecules. Moreover, viminalin I was also synthesized, and its absolute configuration was unambiguously confirmed.

Keywords: syntheses callistrilones; biomimetic syntheses; callistrilones via; via oxidative; oxidative cycloaddition

Journal Title: Organic letters
Year Published: 2018

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