Donor-Acceptor Cyclopropane Ring Expansion to 1,2-Dihydronaphthalenes. Access to Bridged Seven-Membered Lactones

Vitaly V Shorokhov; Sergey S Zhokhov; Victor B Rybakov; Maksim A Boichenko; Ivan A Andreev; Nina K Ratmanova; Igor V Trushkov; Olga A Ivanova

doi:10.1021/acs.orglett.3c02846

Donor-Acceptor Cyclopropane Ring Expansion to 1,2-Dihydronaphthalenes. Access to Bridged Seven-Membered Lactones

Org Lett. 2023 Nov 10;25(44):7963-7967. doi: 10.1021/acs.orglett.3c02846. Epub 2023 Nov 2.

Authors

Vitaly V Shorokhov¹, Sergey S Zhokhov¹, Victor B Rybakov¹, Maksim A Boichenko¹, Ivan A Andreev², Nina K Ratmanova², Igor V Trushkov³, Olga A Ivanova¹

Affiliations

¹ Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie gory 1-3, Moscow 119991, Russia.
² Laboratory of Chemical Synthesis, Dmitry Rogachev National Medical Research Center of Pediatric Hematology, Oncology and Immunology, Samory Mashela 1, Moscow 117997, Russia.
³ N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky pr. 47, Moscow 119991, Russia.

PMID: 37916763
DOI: 10.1021/acs.orglett.3c02846

Abstract

A Lewis-acid-promoted domino ring-opening cyclization of readily available donor-acceptor cyclopropanes with a preinstalled electrophilic center, embedded in a donor group, to functionalized 1,2-dihydronaphthalenes is reported herein. The obtained compounds are transformed to pharmacologically attractive bridged tricyclic esters in a diastereospecific manner.