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Review
. 2021 Dec;33(12):915-930.
doi: 10.1002/chir.23360. Epub 2021 Oct 11.

Reflections on the intriguing occurrence of some recently isolated natural products as racemates and scalemic mixtures

Arie Zask  1 , George A Ellestad  2
Affiliations
Review

Reflections on the intriguing occurrence of some recently isolated natural products as racemates and scalemic mixtures

Arie Zask et al. Chirality. 2021 Dec.

Abstract

This review continues our interest in the intriguing reports of a variety of new racemic natural products (at least 11 in the past 4 years). These include the polyphenolic racemate galewone, the polycyclic prenylated acylphloroglucinol garcinielliptone; variecolortide, a combination of an anthraquinone and a isochinulin-type alkaloid; the isoindoline alkaloid irpexine, the new hybrid phenylproanoid asarone; colletopyandione an indolydenepyradione; the enantiomerically enriched (scalemic) neolignans, gardenifolins; and meroterpenoid pabmaragramin in addition to some marine lipids. We also present a recent biomimetic synthesis of the polyketide preuisolactone A; synthesis of the polyketide spiromamakone A, which also corrected the proposed structure of another metabolite as identical to spiromamakone A; and the melicolones A and B. The continuing reports of natural racemates provoke speculation as to their role in the producing organism.

Keywords: biomimetic syntheses; configurationally unstable metabolites; enantiomerically enriched or scalemic mixtures; racemic natural products.

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References

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