192182-46-0Relevant academic research and scientific papers
Rapid access to spirocyclized indolenines via palladium-catalyzed cascade reactions of tryptamine derivatives and propargyl carbonate
Montgomery, Thomas D.,Nibbs, Antoinette E.,Zhu, Ye,Rawal, Viresh H.
, p. 3480 - 3483 (2014/07/21)
We report the intermolecular palladium-catalyzed reaction of tert-butyl propargyl carbonate with tryptamine derivatives or other indole-containing bis-nucleophiles. The reaction proceeds under mild conditions and with low catalyst loadings to afford novel spiroindolenine products in good to high yields.
Total synthesis of (±)-trigonoliimine C via oxidative rearrangement of an unsymmetrical bis-tryptamine
Qi, Xiangbing,Bao, Hongli,Tambar, Uttam K.
, p. 10050 - 10053 (2011/08/05)
We report the first total synthesis of (±)-trigonoliimine C, a member of a family of structurally complex alkaloids, in 10 steps from tryptamine and 6-methoxytryptamine. Our convergent synthetic strategy relies on a selective oxidative rearrangement of an unsymmetrical 2,2′-bis- tryptamine.
An approach to the hexacyclic skeleton of trigonoliimines
Feng, Pengju,Fan, Yukai,Xue, Fazhen,Liu, Weigang,Li, Songlei,Shi, Yian
, p. 5827 - 5829 (2011/12/22)
A strategy to construct the hexacyclic skeleton of trigonoliimines A, B and their derivatives involving a carbanion-triggered intramolecular cyclization of a seven-membered ring and a subsequent six-membered ring formation in one pot is described.
Intramolecular Formal Aza-[3 + 3] Cycloaddition Approach to Indoloquinolizidine Alkaloids. A Stereoselective Total Synthesis of (±)-Tangutorine
Luo, Shengjun,Zificsak, Craig A.,Hsung, Richard P.
, p. 4709 - 4712 (2007/10/03)
(Equation presented) A 19-step stereoselective total synthesis of (±)-tangutorine is described here. The total synthesis features an intramolecular aza-[3 + 3] formal cycloaddition strategy and also a Heck coupling for constructing the C2-C3 bond. This work provides a novel approach toward the indoloquinolizidine family of alkaloids.
