67199-10-4Relevant articles and documents
Enantioselective Synthesis of 3a-Amino-Pyrroloindolines by Copper-Catalyzed Direct Asymmetric Dearomative Amination of Tryptamines
Liu, Chuan,Yi, Ji-Cheng,Zheng, Zhong-Bo,Tang, Yong,Dai, Li-Xin,You, Shu-Li
, p. 751 - 754 (2016)
A direct asymmetric dearomative amination of tryptamines with O-(2,4-dinitrophenyl)hydroxylamine (DPH) was achieved using CuBr-bisoxazoline complex as a catalyst, affording 3a-amino-pyrroloindolines in good to excellent enantioselectivity under mild reaction conditions. Furthermore, the synthetic value of this method was demonstrated in the total synthesis of (-)-psychotriasine in a highly concise manner. A direct asymmetric dearomative amination of tryptamines with O-(2,4-dinitrophenyl)hydroxylamine (DPH) was achieved using CuBr-bisoxazoline complex as a catalyst, affording 3a-amino-pyrroloindolines in good enantioselectivity under mild reaction conditions. The synthetic value of this method was demonstrated in the total synthesis of (-)-psychotriasine in a highly concise manner.
Structural Revision of Pseudocerosine and Validation of a Biosynthetic Proposal for E-ring Formation in Pyridoacridine Alkaloids
Kim, Se Hun,S?hnel, Tilo,Sperry, Jonathan
supporting information, p. 3495 - 3498 (2020/04/21)
Pseudocerosine is the pigment responsible for the bright blue color of the rim on the marine flatworm Pseudoceros indicus. Compelling evidence is provided herein that pseudocerosine is actually a pyridoacridine, not an azepinoindole as initially proposed. This study also validates a biosynthesis proposal for E-ring formation in this revered class of alkaloids, and pseudocerosine (along with its intermediates described herein) is a new branch on the pyridoacridine family tree.
Lewis Acid Catalyzed Displacement of Trichloroacetimidates in the Synthesis of Functionalized Pyrroloindolines
Adhikari, Arijit A.,Chisholm, John D.
supporting information, p. 4100 - 4103 (2016/08/30)
The pyrroloindoline core is found in many natural products. These structures often differ at the C3a position, which may be substituted with an oxygen, nitrogen, or sp3- or sp2-hybridized carbon. Utilizing a trichloroacetimidate leaving group, a diversity-oriented approach to these structures has been developed. The trichloroacetimidate intermediate allows for the rapid incorporation of anilines, alcohols, thiols, and carbon nucleophiles. This method was applied in the synthesis of arundinine and a formal synthesis of psychotriasine.
