Orthogonal Synthesis of Indolines and Isoquinolines via Aryne Annulation
Described in this report is the development of two unique methodologies exploiting the reactivity of arynes. Reaction of N-carbamoyl-functionalized enamine derivatives with benzyne affords substituted indolines. An orthogonal reactivity is uncovered when related enamine derivatives are modified as amides, such that isoquinolines are formed as the product of condensation with benzyne. This latter transformation is applied to a concise total synthesis of the opiate alkaloid papaverine.
Additional Information© 2008 American Chemical Society. Received 21 October 2007. Published online 15 January 2008. Published in print 1 February 2008. The authors thank Abbott, Amgen, Bristol-Myers Squibb, Merck, and Caltech for generous funding.
Supplemental Material - ja0780582-file003.pdf