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Bioinspired Total Synthesis of Erectones A and B, and the Revised Structure of Hyperelodione D.

ABSTRACT: The field of biomimetic synthesis seeks to apply biosynthetic hypotheses to the efficient construction of complex natural products. This approach can also guide the revision of incorrectly assigned structures. Herein, we describe the evolution of a concise total synthesis and structural reassignment of hyperelodione D, a tetracyclic meroterpenoid derived from a Hypericum plant, alongside some biogenetically related natural products, erectones A and B. The key step in the synthesis of hyperelodione D forms six stereocentres and three rings in a bioinspired cascade reaction that features an intermolecular Diels-Alder reaction, an intramolecular Prins reaction and a terminating cycloetherification.

SUBMITTER: Franov LJ

PROVIDER: S-EPMC9314102 | biostudies-literature | 2022 May

REPOSITORIES: biostudies-literature

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Bioinspired Total Synthesis of Erectones A and B, and the Revised Structure of Hyperelodione D.

Franov Liam J LJ Hart Jacob D JD Pullella Glenn A GA Sumby Christopher J CJ George Jonathan H JH

Angewandte Chemie (International ed. in English) 20220314 19

The field of biomimetic synthesis seeks to apply biosynthetic hypotheses to the efficient construction of complex natural products. This approach can also guide the revision of incorrectly assigned structures. Herein, we describe the evolution of a concise total synthesis and structural reassignment of hyperelodione D, a tetracyclic meroterpenoid derived from a Hypericum plant, alongside some biogenetically related natural products, erectones A and B. The key step in the synthesis of hyperelodio ...[more]

PMID: 35225410

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