An efficient synthetic approach to the tricyclic 1,7a-dihydro-1,3a-ethano-indene and 1,8a-dihydro-1,3a-ethano-azulene skeletons from suitable propargyl vinyl ethers is based on a one-pot, multistep process entailing a gold(I)-catalyzed propargyl Claisen rearrangement/Nazarov cyclization, a [4+2] cycloaddition of the formed six-or seven-membered ring-fused cyclopentadiene system, and a final protection step for the easy isolation and purification of the products by chromatography.
One-Pot Access to 1,7a-Dihydro-1,3a-ethano-indene and 1,8a-Dihydro-1,3a-ethano-azulene Skeletons by a Sequential Gold(I)-Catalyzed Propargyl Claisen Rearrangement/Nazarov Cyclization/[4+2] Cycloaddition Reaction / Rinaldi A.; Lange V.; Scarpi D.; Occhiato E.G.. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 85:(2020), pp. 5078-5086. [10.1021/acs.joc.0c00088]
One-Pot Access to 1,7a-Dihydro-1,3a-ethano-indene and 1,8a-Dihydro-1,3a-ethano-azulene Skeletons by a Sequential Gold(I)-Catalyzed Propargyl Claisen Rearrangement/Nazarov Cyclization/[4+2] Cycloaddition Reaction
Rinaldi A.;Lange V.;Scarpi D.
;Occhiato E. G.
2020
Abstract
An efficient synthetic approach to the tricyclic 1,7a-dihydro-1,3a-ethano-indene and 1,8a-dihydro-1,3a-ethano-azulene skeletons from suitable propargyl vinyl ethers is based on a one-pot, multistep process entailing a gold(I)-catalyzed propargyl Claisen rearrangement/Nazarov cyclization, a [4+2] cycloaddition of the formed six-or seven-membered ring-fused cyclopentadiene system, and a final protection step for the easy isolation and purification of the products by chromatography.
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