Issue 21, 2021
From the journal:

Organic Chemistry Frontiers

Total syntheses of (±)-penicibilaenes A and B via intramolecular aldol condensation†

Rintaro Matsuo,a   Ayumu Watanabe,a   Shogo Kamo, ORCID logo a   Akinobu Matsuzawaa  and  Kazuyuki Sugita ORCID logo *a  

* Corresponding authors

a Department of Synthetic Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan
E-mail: k-sugita@hoshi.ac.jp

Abstract

In this study, concise total syntheses of Peniclillium sesquiterpenes (±)-Penicibilaenes A and B are described. This approach involves an effective intramolecular aldol condensation to construct a bicyclic skeleton, a stereoselective rhodium-catalyzed 1,4-addition, a ring-closing metathesis, and several effective transformations that lead to (±)-penicibilaenes A and B with longest linear sequences of 12 and 13 steps, respectively. These transformations utilize commercial materials and are achieved in 4.0% overall yields for both compounds.

Graphical abstract: Total syntheses of (±)-penicibilaenes A and B via intramolecular aldol condensation

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Article information

DOI
https://doi.org/10.1039/D1QO01251G
Article type
Research Article
Submitted
21 Aug 2021
Accepted
03 Sep 2021
First published
10 Sep 2021

Org. Chem. Front., 2021,8, 6063-6066

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Total syntheses of (±)-penicibilaenes A and B via intramolecular aldol condensation

R. Matsuo, A. Watanabe, S. Kamo, A. Matsuzawa and K. Sugita, Org. Chem. Front., 2021, 8, 6063 DOI: 10.1039/D1QO01251G

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