Issue 4, 2023

Bio-inspired formal total synthesis of (±)-bisabosqual A

Abstract

A new approach was developed to construct a hexahydrobenzofurobenzopyran ring system (6/6/5/6) by an oxa-[3 + 3] cycloaddition, intramolecular hetero-Diels–Alder reaction, oxidative aromatization, and oxidative cyclization cascade starting from 5-(hydroxymethyl)cyclohexane-1,3-dione and (2E,6E)-farnesal. This strategy provides a new solution for preparing tetracyclic hexahydrobenzofurobenzopyran rings with different functional groups at C-3′–C4′. As a synthetic application, the bio-inspired formal total synthesis of bisabosqual A was achieved.

Graphical abstract: Bio-inspired formal total synthesis of (±)-bisabosqual A

Supplementary files

Article information

Article type
Research Article
Submitted
25 Oct 2022
Accepted
04 Jan 2023
First published
19 Jan 2023

Org. Chem. Front., 2023,10, 1042-1046

Bio-inspired formal total synthesis of (±)-bisabosqual A

X. Du, H. Liu, Y. Wu and Y. Tang, Org. Chem. Front., 2023, 10, 1042 DOI: 10.1039/D2QO01697D

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements