Discovery and Total Synthesis of a Bis(cyclotryptamine) Alkaloid Bearing the Elusive Piperidinoindoline Scaffold.

Journal of the American Chemical Society
Jordan J DotsonNeil K Garg

Abstract

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.

References

Jan 1, 1969·Journal of the Chemical Society. Perkin Transactions 1·G W KirbyE J Herbert
Oct 1, 1967·Tetrahedron·E S HallA I Scott
Apr 21, 1998·Journal of Natural Products·L VerottaD S Nunes
Aug 1, 2002·Journal of the American Chemical Society·Alec D LebsackBrian A Stearns
Jun 12, 2003·Angewandte Chemie·Larry E Overman, Emily A Peterson
Jun 12, 2003·Angewandte Chemie·Jeremy J Kodanko, Larry E Overman
Mar 27, 2004·Chemical Communications : Chem Comm·Wei Zhu, Dawei Ma
Apr 7, 2007·Angewandte Chemie·Mohammad Movassaghi, Michael A Schmidt
Jul 28, 2007·Angewandte Chemie·Arunkumar NatarajanMiguel A Garcia-Garibay
Jan 15, 2008·Angewandte Chemie·Mohammad MovassaghiJames A Ashenhurst
Dec 6, 2008·Organic Letters·Kazuhiro HiguchiTomomi Kawasaki
Apr 11, 2009·Science·Justin KimMohammad Movassaghi
Jul 19, 2011·Journal of the American Chemical Society·Mohammad MovassaghiStephen P Lathrop
Sep 16, 2011·Angewandte Chemie·Robert H SnellMichael C Willis
Jan 13, 2015·Journal of the American Chemical Society·María Guadalupe Hernández-LinaresMiguel A Garcia-Garibay
Apr 18, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jin-Biao Xu, Ke-Jun Cheng
Aug 11, 2015·Tetrahedron·Stephen M CanhamLarry E Overman
Sep 12, 2015·Chemistry : a European Journal·Barry M Trost, Maksim Osipov
Sep 25, 2015·The Journal of Organic Chemistry·Ming DingChengfeng Xia
Mar 11, 2016·Journal of the American Chemical Society·Hsiao-Ching LinYi Tang
May 31, 2018·Journal of the American Chemical Society·Jordan J DotsonMiguel A Garcia-Garibay
Aug 20, 2019·Journal of the American Chemical Society·Matthew M PompeoMohammad Movassaghi

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