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Issue 26, 2018
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Biomimetic total syntheses of chromane meroterpenoids, guadials B and C, guapsidial A and psiguajadial D

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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.

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

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Publication details

The article was received on 10 May 2018, accepted on 15 Jun 2018 and first published on 15 Jun 2018


Article type: Communication
DOI: 10.1039/C8OB01092G
Org. Biomol. Chem., 2018,16, 4793-4796

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

    D. H. Dethe, V. K. B. and R. Maiti, Org. Biomol. Chem., 2018, 16, 4793
    DOI: 10.1039/C8OB01092G

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