Total Synthesis of Ulodione A via a Double-Alkylation and DABCO Promoted Ring-Expansion Rearrangement Sequence

Autor:	Chang-Lun Lo, Pavan Sudheer Akula, Bor-Cherng Hong, Gene-Hsiang Lee, Su-Ying Chien
Rok vydání:	2022
Předmět:	Alkylation Molecular Structure Organic Chemistry Physical and Theoretical Chemistry Biochemistry Catalysis Piperazines
Zdroj:	Organic letters. 24(18)
ISSN:	1523-7052
Popis:	First total synthesis of ulodione A has been achieved via the key-step reactions of DIPEA-promoted dialkytion of 1,3-cyclopentadione with a bromonitroolefin and DABCO promoted/catalytic semipinacol-like ring-expansion rearrangement, with regioselective transformation of the nitrocyclohexane intermediates to their cyclopentenone counterparts via a sequence of reactions in a one-pot operation. Structures of six products were unequivocally established by X-ray crystallography.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::6b770be385b34df7f93386f6e4a8ce52 https://pubmed.ncbi.nlm.nih.gov/35499378 Zobrazit plný text záznamu