Welwitindolinone C synthetic studies. Construction of the welwitindolinone carbon skeleton via a transannular nitrone cycloaddition
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چکیده
منابع مشابه
Welwitindolinone C synthetic studies. Construction of the welwitindolinone carbon skeleton via a transannular nitrone cycloaddition.
Described is the construction of the N-methylwelwitindolinone C core via an efficient strategy that employs a sequential rhodium carbenoid-mediated O-H insertion, Claisen rearrangement and transannular [3+2] nitrone cycloaddition.
متن کاملTotal synthesis of (+/-)-welwitindolinone a isonitrile.
A highly stereoselective total synthesis of the alkaloid natural product welwitindolinone A isonitrile has been completed. The synthesis utilizes a chloronium ion mediated semi-pinacol rearrangement to simultaneously install the C10 quaternary center and neopentyl chlorine and a novel anionic cyclization to construct the spiro-oxindole with complete stereocontrol.
متن کاملTransannular nitrone cycloaddition. A stereocontrolled entry to the spirocyclic core of pinnaic acid.
[figure: see text] Thermolysis of lactone 18 initiated a stereospecific transannular nitrone-olefin [3 + 2] cycloaddition to yield tetracycle 19. Methanolysis followed by reductive cleavage of the isoxazolidine yielded 20, representing the azaspirocyclic core of pinnaic acid (1).
متن کاملEvolution of a synthetic strategy: total synthesis of (+/-)-welwitindolinone A isonitrile.
An efficient and highly stereoselective total synthesis of the natural product (+/-)-welwitindolinone A isonitrile (1) is described. The bicyclo[4.2.0]octane core of 1 was established by a regio- and diastereoselective [2+2] ketene cycloaddition. The C12 quaternary center and vicinal stereogenic chlorine were installed in a single operation with excellent stereocontrol via a chloronium ion medi...
متن کاملA mild and efficient synthesis of oxindoles: progress towards the synthesis of welwitindolinone A isonitrile.
Recently, Moore and co-workers reported the isolation and structural elucidation of several oxindole-containing natural products from blue-green algae. Termed the welwitindolinones, this structurally intriguing class of alkaloids displays diverse and valuable biological properties, including multiple drug resistance (MDR) reversing, insecticidal, and antifungal activities. To date, ten congener...
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ژورنال
عنوان ژورنال: Tetrahedron
سال: 2010
ISSN: 0040-4020
DOI: 10.1016/j.tet.2010.04.131