Total Synthesis of (−)-N-Methylwelwitindolinone B Isothiocyanate via a Chlorinative Oxabicycle Ring-Opening Strategy
نویسندگان
چکیده
The first total synthesis of N-methylwelwitindolinone B isothiocyanate is reported. The route features several key steps, including a regio- and diastereoselective chlorinative oxabicycle ring-opening reaction to introduce the challenging alkyl chloride motif.
منابع مشابه
Stereocontrolled synthesis of 20,21-dihydro N-methylwelwitindolinone B isothiocyanate.
Described is a concise synthesis of the 20,21-dihydro analog of N-methylwelwitindolinone B isothiocyanate, wherein a cationic homoallyl to cyclopropylmethyl rearrangement is circumvented by hydrogenation of the offending double bond.
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The synthesis of a functionalized, tetracyclic core of N-methylwelwitindolinone C isothiocyanate is reported. The approach features a convergent coupling between an indole iminium ion and a highly functionalized vinylogous silyl ketene acetal followed by an intramolecular palladium-catalyzed cyclization that proceeds via an enolate arylation.
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As part of a comprehensive strategy to the welwitindolinone alkaloids possessing a bicyclo[4.3.1]decane core, we report herein concise asymmetric total syntheses of (-)-N-methylwelwitindolinone C isothiocyanate (2a), (-)-N-methylwelwitindolinone C isonitrile (2b), and (-)-3-hydroxy-N-methylwelwitindolinone C isothiocyanate (3a) from a common tetracyclic intermediate. The crucial vinyl chloride ...
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