Synthesis of the Bridged [5-7-7] Tricyclic Core of Eurifoloid A

Bao-Long Hou; Li-Xuan Li; Chuang-Chuang Li

doi:10.1021/acs.orglett.1c02784

Synthesis of the Bridged [5-7-7] Tricyclic Core of Eurifoloid A

Org Lett. 2021 Oct 15;23(20):7771-7775. doi: 10.1021/acs.orglett.1c02784. Epub 2021 Sep 23.

Authors

Bao-Long Hou¹, Li-Xuan Li¹, Chuang-Chuang Li¹

Affiliation

¹ Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Shenzhen Grubbs Institute and Department of Chemistry, Southern University of Science and Technology, Shenzhen 518055, China.

PMID: 34554764
DOI: 10.1021/acs.orglett.1c02784

Abstract

We herein describe a new approach for the efficient and asymmetric construction of the tricyclic core of eurifoloid A, which possesses a unique and highly strained bicyclo[4.4.1] ring system. A rhodium-catalyzed intramolecular [3 + 2] dipolar cycloaddition was developed to install synthetically challenging bridged bicyclo[4.3.1] ring systems. The reported chemistry shows the feasibility of constructing the eurifoloid A framework using a diastereoselective intramolecular [3 + 2] cycloaddition and a ring enlargement.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Bridged Bicyclo Compounds / chemical synthesis*
Bridged Bicyclo Compounds / chemistry
Catalysis
Cycloaddition Reaction
Diterpenes / chemical synthesis*
Diterpenes / chemistry
Molecular Structure
Rhodium / chemistry

Substances

Bridged Bicyclo Compounds
Diterpenes
eurifoloid A
Rhodium