Ambient Synthesis of Tricyclic Naphthalenes via Stepwise Styryl-yne Dearomative Diels-Alder Cyclization.
Org Lett
; 23(16): 6536-6541, 2021 Aug 20.
Article
em En
| MEDLINE
| ID: mdl-34369150
ABSTRACT
A cascade of styrylynols promoted by MnO2 allows the synthesis of fused tricycles with a naphthalene core. The reaction occurs under ambient conditions, offering a practical synthetic tool because of the inexpensive and abundant manganese species. The method affords products through the sequential oxidation of a propargyl alcohol, stepwise Diels-Alder cyclization, and finally rearomatization. According to density functional theory, the usually unfavorable stepwise Diels-Alder mechanism is instead a general tool for eliciting otherwise challenging dearomative annulation.
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Coleções:
01-internacional
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MEDLINE
Idioma:
En
Revista:
Org Lett
Ano de publicação:
2021
Tipo de documento:
Article