Total Synthesis of (+)-Coriamyrtin via a Desymmetrizing Strategy Involving a 1,3-Cyclopentanedione Moiety

Kazutada Ikeuchi; Shota Haraguchi; Ryo Fujii; Hidetoshi Yamada; Takahiro Suzuki; Keiji Tanino

doi:10.1021/acs.orglett.3c00249

Total Synthesis of (+)-Coriamyrtin via a Desymmetrizing Strategy Involving a 1,3-Cyclopentanedione Moiety

Org Lett. 2023 Apr 28;25(16):2751-2755. doi: 10.1021/acs.orglett.3c00249. Epub 2023 Feb 28.

Authors

Kazutada Ikeuchi¹, Shota Haraguchi², Ryo Fujii³, Hidetoshi Yamada², Takahiro Suzuki¹, Keiji Tanino¹

Affiliations

¹ Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan.
² School of Science and Technology, Kwansei Gakuin University, Sanda 669-1337, Japan.
³ School of Science, Hokkaido University, Sapporo 060-0810, Japan.

PMID: 36853202
DOI: 10.1021/acs.orglett.3c00249

Abstract

We describe the total synthesis of (+)-coriamyrtin, which bears a highly functionalized cis-hydrindane skeleton and is a widely known neurotoxin of the Coriariaceae family. Our synthetic strategy involves the highly stereoselective construction of the cis-hydrindane skeleton via a desymmetrizing strategy involving a 1,3-cyclopentanedione moiety using an intramolecular aldol reaction and the formation of the 1,3-diepoxide moiety of coriamyrtin through the elaborate functionalization of the cyclopentane ring in the bicyclic structure.