ChemInform Abstract: Al-Catalyzed Facile Construction of Quaternary C-C Bonds by the Allylic Substitution of Tertiary Alcohols: A Concise and Formal Synthesis of (.+-.)-Mersicarpine.
Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun, Jilin 130022, China.Chemistry - A European Journal (Impact Factor: 5.73). 01/2013; 18(32):9784-8. DOI: 10.1002/chem.201201344
In close quarters: A concise, high-yielding, and more sustainable route for the synthesis of (±)-mersicarpine in nine linear steps from commercially available indole and succinic anhydride is presented. It is also demonstrated that the novel protocol can be commonly used for the rapid and flexible construction of a diverse class of mersicarpine analogues.
Article: Total syntheses of mersicarpine[Show abstract] [Hide abstract]
ABSTRACT: This review focuses on synthetic studies on mersicarpine that has a characteristic skeleton including seven-membered cyclic imine fused with indoline and δ-lactam. After a brief discussion of structural features and proposed biogenesis of this compound, several synthetic efforts toward construction of mersicarpine core are described. Total syntheses of mersicarpine are described including Kerr's racemic synthesis utilizing a formation of seven-membered cyclic imine from α-hydroxyketone prepared by oxidation of indole, racemic syntheses of the Kerr's synthetic intermediate by Zard and Han, the first enantiocontrolled total synthesis by Fukuyama based on the construction of seven-membered α-hydroxyimine by autoxidation of azepinoindole, and the second enantiocontrolled synthesis by Tokuyama employing a DIBALH-mediated ring-expansion reaction of cyclic ketoxime fused with indole.
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ABSTRACT: A quick access to the core of dihydroindole alkaloid mersicarpine was developed based on straightforward transformations from readily available and inexpensive starting materials. The synthetic route features an aldol reaction, a Beckmann rearrangement for the synthesis of the δ-lactam, an intramolecular SNAr strategy for indoxyl heterocycle formation, and in situ autoxidation of indoxyl intermediate. The new strategy offered an alternative approach for the formation of an oxidized indoxyl moiety, which could potentially have a wider application in the total synthesis of indole alkaloids containing apparent or masked indoxyl moieties.Tetrahedron Letters 01/2013; 54(3):242–244. DOI:10.1016/j.tetlet.2012.11.008 · 2.38 Impact Factor
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ABSTRACT: The formal syntheses of N-methylwelwitindolinone C isothiocyanate (4) and several other welwitindolinones 5-8 were achieved by the independent synthesis of 79. The synthesis featured a Lewis acid-mediated coupling between a heteroaryl carbinol and bis-TMS enol ether, an intramolecular enolate arylation, and an unprecedented intramolecular allylic alkylation of a γ-acyloxyenone.Tetrahedron 07/2013; 69(27-28):5588-5603. DOI:10.1016/j.tet.2013.03.010 · 2.64 Impact Factor
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