Published February 6, 2008
| Supplemental Material
Journal Article
Open
Orthogonal Synthesis of Indolines and Isoquinolines via Aryne Annulation
Abstract
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.Attached Files
Supplemental Material - ja0780582-file003.pdf
Files
ja0780582-file003.pdf
Files
(445.1 kB)
| Name | Size | Download all |
|---|---|---|
|
md5:f511852a0bf87e249e239aa56f727e33
|
445.1 kB | Preview Download |
Additional details
- Eprint ID
- 74512
- DOI
- 10.1021/ja0780582
- Resolver ID
- CaltechAUTHORS:20170223-153451419
- Abbott
- Amgen
- Bristol-Myers Squibb
- Merck
- Caltech
- Created
-
2017-02-24Created from EPrint's datestamp field
- Updated
-
2021-11-11Created from EPrint's last_modified field