Ready Access to the Echinopines Skeleton via Gold(I)-Catalyzed Alkoxycyclizations of Enynes | Zendy

Ruth Dorel | Zendy; Antonio M. Echavarren | Zendy

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Ready Access to the Echinopines Skeleton via Gold(I)-Catalyzed Alkoxycyclizations of Enynes

Author(s) -

Ruth Dorel,

Antonio M. Echavarren

Publication year - 2016

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.6b01607

Subject(s) - enyne , chemistry , nonane , cycloaddition , catalysis , bicyclic molecule , skeleton (computer programming) , stereochemistry , core (optical fiber) , combinatorial chemistry , organic chemistry , computer science , programming language , materials science , composite material

The [3,5,5,7] tetracyclic skeleton of echinopines has been stereoselectively accessed through a gold(I)-catalyzed alkoxycyclization of cyclopropyl-tethered 1,6-enynes. The key bicyclo[4.2.1]nonane core of the enyne precursors was readily assembled by means of a Co-catalyzed [6 + 2] cycloaddition. Furthermore, the attempted alkoxycyclization of 1,5-enyne substrates revealed an uncovered cyclopropyl rearrangement that gives rise to [3,6,5,7] tetracyclic structures.

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