56267-47-1Relevant articles and documents
Synthetic methodology to prepare polysubstituted 2-aminopyrans. Synthesis of the C32–C38 subunit of immunosuppressant sanglifehrin A
Monta?a, ángel M.,Barcia, Joan,Corominas, Albert
, p. 4798 - 4812 (2016)
Pyranic hemiaminal synthons are present in natural and unnatural products with biological activity. Here a synthetic pathway to prepare this type of intermediates is presented. The methodology is based on three main steps: a) The [4+3] cycloaddition reaction of an α,α'-dihaloketone and a conveniently protected 2-aminofuran diene. b) Chemical modification of the resulting oxabicyclic cycloadduct and orthogonal protection of organic functions, and c) Reductive ozonolysis of the C6–C7 double bond of the modified cycloadduct to afford a pentasubstituted polyfunctionalized pyranic hemiaminal ester with up to 94% yield. When working with 2,4-dibromo-3-pentanone and 2-tert-butoxycarbonylaminofuran as starting materials, the C32–C38 subunit of immunosuppressant sanglifehrin A was obtained with excellent yield.
Formation of 6-Azaindoles by Intramolecular Diels-Alder Reaction of Oxazoles and Total Synthesis of Marinoquinoline A
Jhaveri, Dishit P.,Osano, Mana,Wipf, Peter
supporting information, p. 2215 - 2219 (2020/04/09)
A new variant of the intramolecular Diels-Alder oxazole (IMDAO) cycloaddition that provides direct access to 6-azaindoles was developed. The IMDAO reaction was applied in a total synthesis of the aminophenylpyrrole-derived alkaloid marinoquinoline A, also
Indole synthesis by palladium-catalyzed tandem allylic isomerization-furan Diels-Alder reaction
Xu, Jie,Wipf, Peter
supporting information, p. 7093 - 7096 (2017/09/07)
A Pd(0)-catalyzed elimination of an allylic acetate generates a π-allyl complex that is postulated to initiate a novel intramolecular Diels-Alder cycloaddition to a tethered furan (IMDAF). Under the reaction conditions, this convergent, microwave-accelerated cascade process provides substituted indoles in moderate to good yields after Pd-hydride elimination, aromatization by dehydration, and in situ N-Boc cleavage.
