Issue 19, 2020

Photoinduced double [2 + 2] cycloaddition relay of yne–allenones for highly diastereoselective synthesis of hexacyclic 1-naphthols

Abstract

A new photoinduced photocatalyst-free energy-transfer strategy for double [2 + 2] cycloaddition relay of yne–allenones is reported for the first time and used to produce a series of hitherto unreported hexacyclic 1-naphthols with good yields and complete diastereoselectivity. The reaction pathway generates a class of complex three-dimensional structures with two all-carbon quaternary centers evolved from the planar conjugated system through cleavage and recombination of the C–C triple bond of yne–allenones, enabling the direct formation of four new rings in one step.

Graphical abstract: Photoinduced double [2 + 2] cycloaddition relay of yne–allenones for highly diastereoselective synthesis of hexacyclic 1-naphthols

Supplementary files

Article information

Article type
Research Article
Submitted
29 Jul 2020
Accepted
27 Aug 2020
First published
28 Aug 2020

Org. Chem. Front., 2020,7, 2975-2980

Photoinduced double [2 + 2] cycloaddition relay of yne–allenones for highly diastereoselective synthesis of hexacyclic 1-naphthols

S. Zhu, J. Zhou, Q. Wu, W. Hao, S. Tu and B. Jiang, Org. Chem. Front., 2020, 7, 2975 DOI: 10.1039/D0QO00917B

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