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Published November 26, 2008 | Supplemental Material
Journal Article Open

A concise total synthesis of (−)-quinocarcin via aryne annulation


Described in this report is a rapid asymmetric total synthesis of the tetrahydroisoquinoline antitumor antibiotic (−)-quinocarcin. The sequence employs a mild fluoride-induced aryne annulation developed in our laboratories to build a key isoquinoline-containing intermediate comprising the entire carbon scaffold of the natural product. This intermediate is advanced through six additional steps to the target alkaloid, providing the shortest synthetic route to (−)-quinocarcin reported to date.

Additional Information

© 2008 American Chemical Society. Received October 14, 2008; E-mail: stoltz@caltech.edu. The authors thank Abbott, Amgen, Boehringer- Ingelheim, Bristol-Myers Squibb, Merck, Sigma-Aldrich, and Caltech for generous funding. Special thanks to Dr. Scott C. Virgil of the Caltech Center for Catalysis and Chemical Synthesis for helpful discussions.

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Supplemental Material - ja808112y_si_001.pdf


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