Open AccessStudies Targeting Ryanodol Result in an Annulation Reaction for the Synthesis of a Variety of Fused Carbocycles
Author(s) -
Rajdip Karmakar,
Arnold L. Rheingold,
Glenn C. Micalizio
Publication year - 2019
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.9b02278
Subject(s) - annulation , chemistry , context (archaeology) , reagent , combinatorial chemistry , alkyne , coupling reaction , ring (chemistry) , stereochemistry , organic chemistry , paleontology , biology , catalysis
An annulation reaction is described to access a range of polycyclic and highly oxygenated carbocycles. First developed in an approach to the synthesis of ryanodol, metallacycle-mediated annulative diketone-alkyne coupling defines a framework for realization of new retrosynthetic relationships for complex molecule synthesis. In addition to demonstrating this reaction in the context of forging distinct carbocyclic systems, including those featuring a seven-membered ring, the choice of quenching reagent leads to unique reaction outcomes.