Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 142, Issue 27, Pages 11685-11690Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c04760
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Funding
- National Science Foundation [CHE-1855342]
- UCLA Graduate Division
- NSF [CHE-1048804]
- National Center for Research Resources [S10RR025631]
- Trueblood Family
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Bis(cyclotryptamine) alkaloids have been popular topics of study for many decades. Five possible scaffolds for bis(cyclotryptamine) alkaloids were originally postulated in the 1950s, but only four of these scaffolds have been observed in natural products to date. We describe synthetic access to the elusive fifth scaffold, the piperidinoindoline, through syntheses of compounds now termed dihydropsychotriadine and psychotriadine. The latter of these compounds was subsequently identified in extracts of the flower Psychotria colorata. Our synthetic route features a stereospecific solid-state photodecarbonylation reaction to introduce the key vicinal quaternary stereocenters.
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