Biomimetic total syntheses of chromane meroterpenoids, guadials B and C, guapsidial A and psiguajadial D

Literature Information

Publication Date 2018-06-15
DOI 10.1039/C8OB01092G
Impact Factor 3.876
Authors

Dattatraya H. Dethe, Vijay Kumar B., Rakesh Maiti


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Abstract

The first biomimetic total syntheses of chromane meroterpenoids, guadials B and C, guapsidial A and psiguajadial D have been completed. The key synthetic transformation involves an efficient and high yielding hetero-Diels–Alder reaction. The two structurally isomeric natural products, guadials B and C, were obtained from a common o-quinone methide in the separate reactions with α-pinene and β-pinene, respectively. The two regioisomeric natural products, guapsidial A and psiguajadial D, were achieved in a single chemical operation.

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Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
CiteScore: 3.4
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Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

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