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Zask A, Ellestad GA. Reflections on the intriguing occurrence of some recently isolated natural products as racemates and scalemic mixtures. Chirality. 2021;33(12):915-930doi: 10.1002/chir.23360.
Zask, A., & Ellestad, G. A. (2021). Reflections on the intriguing occurrence of some recently isolated natural products as racemates and scalemic mixtures. Chirality, 33(12), 915-930. https://doi.org/10.1002/chir.23360
Zask, Arie, and Ellestad, George A. "Reflections on the intriguing occurrence of some recently isolated natural products as racemates and scalemic mixtures." Chirality vol. 33,12 (2021): 915-930. doi: https://doi.org/10.1002/chir.23360
Zask A, Ellestad GA. Reflections on the intriguing occurrence of some recently isolated natural products as racemates and scalemic mixtures. Chirality. 2021 Dec;33(12):915-930. doi: 10.1002/chir.23360. Epub 2021 Oct 11. PMID: 34633708.
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Chirality. 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.

Chirality

Arie Zask, George A Ellestad

Affiliations

  1. Department of Biological Sciences, Columbia University, New York, NY, USA.
  2. Department of Chemistry, Columbia University, New York, NY, USA.

PMID: 34633708 DOI: 10.1002/chir.23360

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.

© 2021 Wiley Periodicals LLC.

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

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