Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 18, Pages 8954-8967Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b00872
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Funding
- National Science Foundation [CHE-0955864, CHE-1464898, DGE-1144087]
- Boehringer Ingelheim
- DuPont
- Bristol-Myers Squibb
- S. T. Li Foundation
- Dreyfus Foundation
- A. P. Sloan Foundation
- University of California, Los Angeles
- UCLA Graduate Division for a Dissertation Year Fellowship
- NIH-NIGMS [F31-GM113642]
- NSF [CHE-1048804]
- National Center for Research Resources [S10RR025631]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1464898] Funding Source: National Science Foundation
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Picrinine, which is a member of the akuammiline family of alkaloids, was first isolated in 1965 from the leaves of Alstonia scholaris. The natural product possesses a daunting polycyclic skeleton that contains a furanoindoline, a bridged [3.3.1]azabicycle, two N,O-acetal linkages, and six stereogenic centers. These structural features render picrinine a challenging and attractive target for total synthesis. This paper provides a full account of our synthetic forays toward picrinine, which culminates in the first total synthesis of this long-standing target. Central to the success of our approach is the use of the Fischer indolization reaction to introduce the C7 quaternary stereocenter and the indoline nucleus of the natural product's scaffold. We probe some of the subtleties of this classic transformation by examining some of the most complex Fischer indolization substrates to date. Additionally, we describe various roadblocks encountered in our experimental efforts, which were successfully overcome to complete the total synthesis of picrinine.
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