Unified Approach for the Total Synthesis of Bis-THF C₁₅ Acetogenins: A Chloroenyne from Laurencia majuscula, Laurendecumenyne B and Laurefurenynes A/B

Abstract

A highly diastereoselective total synthesis of several bis-THF C₁₅ acetogenin natural products, chloroenyne from Laurencia majuscula, laurendecumenyne B, and laurefurenynes A/B, is reported. Additionally the synthesis of an advanced intermediate reported in the earlier total synthesis of (E/Z)-elatenynes (formal synthesis) is described. The salient features in the synthesis include epoxide opening, Birch reduction, Sharpless asymmetric dihydroxylation-cycloetherification, S_N2 halo­genation, and a relay cross metathesis.

Key words

bis-THF C₁₅ acetogenins - carbohydrate building block - Sharpless asymmetric dihydroxylation-cycloetherification - S_N2 halo­genation - relay-cross-metathesis

Publikationsverlauf

Eingereicht: 09. April 2021

Angenommen nach Revision: 05. Mai 2021

Accepted Manuscript online:
05. Mai 2021

Artikel online veröffentlicht:
02. Juni 2021

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