Issue 26, 2018

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

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

Supplementary files

Article information

Article type
Communication
Submitted
10 Mai 2018
Accepted
15 Jun 2018
First published
15 Jun 2018

Org. Biomol. Chem., 2018,16, 4793-4796

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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