The synthesis of (±)-epi-jungianol was successfully carried out by the gold(I)-catalyzed propargyl Claisen rearrangement/hydroarylation cascade reaction of suitably substituted propargyl vinyl ethers as the key step to form the indane skeleton. Two routes were compared, which involved substrates with a different degree of substitution on the vinyl moiety. The one based on a propargyl vinyl ether bearing an unsubstituted vinyl moiety, despite entailing two additional steps, provided the final compound in a higher overall yield. A method for the preparation of acid sensitive propargyl vinyl ethers with an α-alkyl-substituted vinyl moiety and their reactivity under gold catalysis is also reported.
Synthesis of (±)-epi-Jungianol by the Gold(I)-Catalyzed Propargyl Claisen Rearrangement/Hydroarylation Cascade Reaction of Propargyl Vinyl Ethers / Rinaldi A.; Lange V.; Scarpi D.; Occhiato E.G.. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - 2021:(2021), pp. 1266-1273. [10.1002/ejoc.202001555]
Synthesis of (±)-epi-Jungianol by the Gold(I)-Catalyzed Propargyl Claisen Rearrangement/Hydroarylation Cascade Reaction of Propargyl Vinyl Ethers
Rinaldi A.;Scarpi D.;Occhiato E. G.
2021
Abstract
The synthesis of (±)-epi-jungianol was successfully carried out by the gold(I)-catalyzed propargyl Claisen rearrangement/hydroarylation cascade reaction of suitably substituted propargyl vinyl ethers as the key step to form the indane skeleton. Two routes were compared, which involved substrates with a different degree of substitution on the vinyl moiety. The one based on a propargyl vinyl ether bearing an unsubstituted vinyl moiety, despite entailing two additional steps, provided the final compound in a higher overall yield. A method for the preparation of acid sensitive propargyl vinyl ethers with an α-alkyl-substituted vinyl moiety and their reactivity under gold catalysis is also reported.File | Dimensione | Formato | |
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