C (2)-Functionalized tryptophans from 3-acetoxyindoles and their possible implication in indole alkaloid biosynthesis

R Plate, AWG Theunisse… - The Journal of Organic …, 1987 - ACS Publications
The acetoxyindoles 10 and 11 are efficiently converted (85-95%) into the dihydro-1, 2-
oxazines 13 and 14, respectively, by reaction with the transient nitroso olefin 2, prepared in …

Synthesis of 3-(indol-2-yl)-propenoate derivatives of tryptamine, valuable intermediates for the preparation of indole alkaloids

PD Bailey, SP Hollinshead - Tetrahedron letters, 1987 - Elsevier
Tetrahedron Letters,Vol.28,No.25,pp 2879-2882,1987 0040-4039/87 $3.00 + .OO Printed in
Great Britain Pergamon Journals Ltd. SYNT Page 1 Tetrahedron Letters,Vol.28,No.25,pp …

Synthetic approaches to 3-(2-nitroalkyl) indoles and their use to access tryptamines and related bioactive compounds

S Lancianesi, A Palmieri, M Petrini - Chemical Reviews, 2014 - ACS Publications
The assembly of architecturally complex alkaloids embedding the indole nucleus is of
paramount importance for the target oriented synthesis of biologically active molecules. 1 A …

Electrophilic substitution in indoles—II: The formation of 3, 3-spirocyclic indole derivatives from tryptamines and their rearrangement to β-carbolines

AH Jackson, AE Smith - Tetrahedron, 1968 - Elsevier
Attempts to isolate 3, 3-spiro-cyclicindolenines thought to be intermediates in the cyclization
of benzylidenetryptamines to tetrahydro-β-carbolines are described. One such spiro …

Stereoselective oxidative rearrangement of 2-aryl tryptamine derivatives.

M Movassaghi, MA Schmidt, JA Ashenhurst - Organic Letters, 2008 - europepmc.org
The oxidation of 2-aryl tryptamines followed by a stereoselective rearrangement provides a
versatile strategy for the synthesis of C3-quaternary oxindoles bearing a C3-aryl group …

Chemistry of the Hexahydropyrrolo[2,3-b]indoles:  Configuration, Conformation, Reactivity, and Applications in Synthesis

D Crich, A Banerjee - Accounts of chemical research, 2007 - ACS Publications
The stereoselective formation of 2-endo-substituted hexahydropyrrolo [2, 3-b] indoles from 2-
substituted tryptamine derivatives, especially tryptophan, is discussed. Parallels are drawn …

Recent advances in the chemistry of 1-hydroxyindoles, 1-hydroxytryptophans, and 1-hydroxytryptamines

M Somei - 2002 - Elsevier
We have thus far provided the groundwork for investigations of 1-hydroxy-and 1-
alkoxyindoles and 1-hydroxytryptophans and-tryptamines, and discovered that they undergo …

Synthetic studies on indole alkaloids. VII. Effect of the piperidine ring substitution on intramolecular KtBuO/BF3. Et2O cyclization of N-(2-hydroxyethyl)-2-[1 …

A Diez, C Villa, M Rubiralta - Tetrahedron, 1993 - Elsevier
3, 3-Disubstituted N-(2-hydroxyethyl)-2-[1-(phenylsulfonyl)-3-indolyl]-piperidine 4 shows a
particular reactivity in front of KtBuO/BF3. Et2O: the intermediate spiroindolenine 15 evolves …

Synthetic Studies toward 1,2,3,3a,4,8b-Hexahydropyrrolo[3,2-b]indole Core. Unusual Fragmentation with 1,2-Aryl Shift

AV Aksenov, EV Aleksandrova… - The Journal of …, 2022 - ACS Publications
Base-assisted transformations of 2-(3-oxoindolin-2-yl) acetonitriles were investigated.
Unexpectedly, attempted reactions of substrates possessing nonprotected nitrogen atoms …

Novel Products from Bischler-Napieralski Reaction of Arylacetyl-Tryptophan Esters. Synthesis of Spiropentacyclic Indolines Structurally Related to Indole Alkaloids

KM Biswas, RN Dhara, S Halder, H Mallik… - Synthetic …, 1993 - Taylor & Francis
Novel Products from Bischler-Napieralski Reaction of Arylacetyl-Tryptophan Esters. Synthesis of
Spiropentacyclic Indolines Struc Page 1 SYNTHETIC COMMUNICATIONS, 23(3), 379-388 (1993) …