Results 121 to 130 of about 174 (166)

Enantioselective total synthesis of the indole alkaloid 16-episilicine

Chemical Communications, 2009
The first total synthesis of (-)-16-episilicine has been completed from a phenylglycinol-derived bicyclic lactam, the key steps being stereoselective conjugate addition and alkylation reactions, and a ring-closing metathesis.
Mercedes, Amat, Begoña, Checa, Núria, Llor, Elies, Molins, Joan, Bosch   +4 more
openaire   +2 more sources

Tremorgenic Indole Alkaloids. The Total Synthesis of (−)-Penitrem D

Journal of the American Chemical Society, 2003
A convergent, stereocontrolled total synthesis of the architecturally complex tremorgenic indole alkaloid (-)-penitrem D (4) has been achieved. Highlights of the synthesis include an efficient, asymmetric synthesis of the western hemisphere; the stereocontrolled assembly of the I-ring; discovery of a novel autoxidation to introduce the C(22) tertiary ...
Amos B, Smith, Naoki, Kanoh, Haruaki, Ishiyama, Noriaki, Minakawa, Jon D, Rainier, Richard A, Hartz, Young Shin, Cho, Haifeng, Cui, William H, Moser   +8 more
openaire   +2 more sources

Total Synthesis of Sarpagine‐Related Bioactive Indole Alkaloids

Chemistry – A European Journal, 2018
AbstractExtension of the asymmetric Pictet–Spengler reaction to bulkier Nb‐alkylated tryptophan derivatives resulted in an improved stereospecific access to the key bicyclo[3.3.1]nonane core of bioactive C‐19 methyl substituted sarpagine/macroline/ajmaline indole alkaloids with excellent diastereoselectivity by internal asymmetric induction.
M. Toufiqur Rahman, Jeffrey R. Deschamps, Gregory H. Imler, James M. Cook   +3 more
openaire   +2 more sources

Formal Total Synthesis of Diazonamide A by Indole Oxidative Rearrangement

Chemistry – A European Journal, 2016
AbstractA short formal total synthesis of the marine natural product diazonamide A is described. The route is based on indole oxidative rearrangement, and a number of options were investigated involving migration of tyrosine or oxazole fragments upon oxidation of open chain or macrocyclic precursors.
Nadège David, Raffaele Pasceri, Russell R. A. Kitson, Alexandre Pradal, Christopher J. Moody   +4 more
openaire   +2 more sources

First Total Synthesis of Trimeric Indole Alkaloid, Psychotrimine

Organic Letters, 2007
The first total synthesis of (+/-)-psychotrimine, a novel trimeric indole alkaloid isolated from Psychotria rostrata, was achieved. In the total synthesis, the copper-mediated intramolecular and intermolecular aminations of halobenzenes, which respectively contributed to the construction of a pyrrolidinoindoline core and the installation of a third ...
Yohei, Matsuda, Mariko, Kitajima, Hiromitsu, Takayama   +2 more
openaire   +2 more sources

Fischer Indolizations as a Strategic Platform for the Total Synthesis of Picrinine

The Journal of Organic Chemistry, 2015
Picrinine, which is a member of the akuammiline family of alkaloids, was first isolated in 1965 from the leaves of Alstonia scholaris. The natural product possesses a daunting polycyclic skeleton that contains a furanoindoline, a bridged [3.3.1]azabicycle, two N,O-acetal linkages, and six stereogenic centers.
Joel M, Smith, Jesus, Moreno, Ben W, Boal, Neil K, Garg   +3 more
openaire   +2 more sources

A Divergent Enantioselective Total Synthesis of Post‐Iboga Indole Alkaloids

Angewandte Chemie International Edition, 2020
AbstractDivergent enantioselective total syntheses of five naturally occurring post‐iboga indole alkaloids, dippinine B and C, 10,11‐demethoxychippiine, 3‐O‐methyl‐10,11‐demethoxychippiine, and 3‐hydroxy‐3,4‐secocoronaridine, as well as the two analogues 11‐demethoxydippinine A and D, are presented for the first time.
Jie Zhou, Dong‐Xing Tan, Fu‐She Han
openaire   +2 more sources

Total synthesis of the indole alkaloids henrycinol A and B

Tetrahedron, 2014
Abstract The total synthesis of new indole alkaloids henrycinol A and B were accomplished starting from l -tryptophan methyl ester. The key step is a stereochemically flexible Pictet–Spengler reaction governed by the presence or absence of an N-allyl group in the tryptophan precursor.
Kavirayani R. Prasad, John Eugene Nidhiry, Makuteswaran Sridharan   +2 more
openaire   +1 more source

Recent progress in the total synthesis of indole alkaloids.

Current opinion in drug discovery & development, 2010
This review describes the most recent synthetic routes directed toward the construction of structurally complex indole alkaloids, many syntheses of which contain the asymmetric Pictet-Spengler reaction as a key stereochemical step. A kinetic and conformational study of the epimerization of cis 1,2,3-trisubstituted tetrahydro-beta-carbolines into their ...
Chitra R, Edwankar, Rahul V, Edwankar, Ojas A, Namjoshi, Sundari K, Rallapalli, Jie, Yang, James M, Cook   +5 more
openaire   +2 more sources

Construction of cyclohepta[b]indoles in the total synthesis of indole alkaloids

2017
[no abstract]
openaire   +1 more source