Biomimetic Synthesis of (±)-Merochlorin B

Biomimetic Synthesis of (±)-Merochlorin B

A short total synthesis, guided by biosynthetic considerations, of racemic merochlorin B is presented. The formation of its isomer, merochlorin A, was not observed under the conditions. Key steps include a directed ortho-metalation (DoM), a selective demethylation, an ortho-allylation, and an oxidat...

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Veröffentlicht in:Organic letters 2014-05, Vol.16 (10), p.2634-2637
Hauptverfasser: Meier, Robin, Strych, Sebastian, Trauner, Dirk
Format: Artikel
Sprache:eng
Schlagworte:
Biomimetics
Cycloaddition Reaction
Indicators and Reagents
Iodine - chemistry
Molecular Structure
Oxidation-Reduction
Sesterterpenes - chemical synthesis
Sesterterpenes - chemistry
Stereoisomerism
Streptomyces - chemistry
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Zusammenfassung:A short total synthesis, guided by biosynthetic considerations, of racemic merochlorin B is presented. The formation of its isomer, merochlorin A, was not observed under the conditions. Key steps include a directed ortho-metalation (DoM), a selective demethylation, an ortho-allylation, and an oxidative [3 + 2]-cycloaddition mediated by an iodine­(III) reagent.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol500800z