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: firstname.lastname@example.org. 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.
Supplemental Material - ja808112y_si_001.pdf