Total Synthesis of (±)-Integrifolin

Katsuya Shimomaki; Hiroyuki Kusama; Nobuharu Iwasawa

doi:10.1002/chem.201601275

Total Synthesis of (±)-Integrifolin

Chemistry. 2016 Jul 11;22(29):9953-7. doi: 10.1002/chem.201601275. Epub 2016 Jun 13.

Authors

Katsuya Shimomaki¹, Hiroyuki Kusama^{1

2}, Nobuharu Iwasawa³

Affiliations

¹ Department of Chemistry, Tokyo Institute of Technology, 2-12-1, O-okayama, Meguro-ku, Tokyo, 152-8851, Japan.
² Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1, Mejiro, Toshima-ku, Tokyo, 171-8588, Japan.
³ Department of Chemistry, Tokyo Institute of Technology, 2-12-1, O-okayama, Meguro-ku, Tokyo, 152-8851, Japan. niwasawa@chem.titech.ac.jp.

PMID: 27147582
DOI: 10.1002/chem.201601275

Abstract

The total synthesis of (±)-integrifolin has been achieved for the first time through the stereoselective preparation of the bicyclo[5.3.0]decane skeleton based on the tungsten-catalyzed cyclization of acyclic trienynes under photoirradiation conditions. Further key transformations of the cyclized product are the Tamao oxidation through cyclic silyl ether, the introduction of two oxygen functionalities by the oxidation of the diene and the construction of three exo-methylene moieties.

Keywords: alkenes; cyclization; sesquiterpenoids; total synthesis; tungsten.

MeSH terms

Alkenes / chemical synthesis*
Catalysis
Cyclization
Ethers / chemistry*
Molecular Structure
Oxidation-Reduction

Substances

Alkenes
Ethers