Total synthesis of tryprostatin A and B as well as their enantiomers
Tetrahedron LettersPublished 1 September 1998
Shuo Zhao, Tong J. Gan, Yu Peng, James M. Cook
Citations39
SJR quartileQ3
SJR score0.33
SNIP0.43
Generate an AI Snapshot to get a quick, structured summary of this paper.
Study Snapshot
ObjectiveStudy objective
MethodsResearch methodology
PopulationPopulation studied
Sample sizeSample sizes
OutcomesStudy outcomes here
ResultsStudy results comes here
LimitationsResearch study limitations comes here
A concise AI-generated summary of the paper will appear here once you click Generate AI Snapshot.
Abstract
The 3-methylindoles 3a, 3b were converted into tryprostatin A (1a), B (1b) and their enantiomers 2a, 2b via prenylation at the indole 2-position by generation of the required 2-lithioindole derivatives (from 7a, 7b), followed by alkylation.
Keywords
ChemistryBiochemistry, Genetics and Molecular Biology
Fortschritte der Chemie Organischer Naturstoffe/Fortschritte der Chemie organischer Naturstoffe/Progress in the chemistry of organic natural productsProgress in the Chemistry of Organic Natural Products 109
2,053 Citations2019A. Douglas Kinghorn, Heinz Falk +4 more
The Journal of AntibioticsNovel Mammalian Cell Cycle Inhibitors, Tryprostatins A, B and Other Diketopiperazines Produced by Aspergillus fumigatus. I. Taxonomy, Fermentation, Isolation and Biological Properties.
207 Citations1996Cheng‐Bin Cui, Hideaki Kakeya +3 more
The diketopiperazines showed an inhibitory activity on the cell cycle progression of mouse tsFT210 cells in the M phase with the MIC values of 16.4 microM and 12.2 microM, respectively.
The Journal of Organic ChemistryGeneration and reactions of 3-lithio-1-(phenylsulfonyl)indole
170 Citations1982Mark G. Saulnier, Gordon W. Gribble
The Journal of AntibioticsNovel Mammalian Cell Cycle Inhibitors, Tryprostatins A, B and Other Diketopiperazines Produced by Aspergillus fumigatus. II. Physico-chemical Properties and Structures.
148 Citations1996Cheng‐Bin Cui, Hideaki Kakeya +1 more
The structures of tryprostatins A, B and demethoxyfumitremorgin C were determined mainly by the use of spectroscopic methods especially by detailed analyses of their 1H and 13C NMR spectra with the aid of 2D NMR techniques including pulse field gradient heteronuclear multiple-bond correlation (PFG-HMBC) spectroscopy.
Journal of the American Chemical SocietyTotal Synthesis of Tryprostatin B: Generation of a Nucleophilic Prenylating Species from a Prenylstannane
84 Citations1996Kristopher M. Depew, Samuel J. Danishefsky +2 more
Synthetic CommunicationsEntry into 6-Methoxy-D(+)-tryptophans. Stereospecific Synthesis of 1-Benzenesulfonyl-6-methoxy-D(+)-tryptophan Ethyl Ester
69 Citations1992M.S. Allen, Linda K. Hamaker +2 more
The Journal of Organic ChemistryRapid continuous peptide synthesis via FMOC amino acid chloride coupling and 4-(aminomethyl)piperidine deblocking
64 Citations1990Michael Beyermann, Michael Bienert +3 more
The recently described FMOC/4-AMP technique for rapid continuous solution synthesis of peptides involving coupling by crystalline FMOC amino acid chlorides and deblocking via 4-(aminomethyl)piperidine ( 4-AMP) has been extended to the synthesis of a varied number of tachykinin peptides.
The Journal of Organic ChemistryEnantiospecific Synthesis of Optically Active 6-Methoxytryptophan Derivatives and Total Synthesis of Tryprostatin A<sup>1</sup>
58 Citations1997Tong J. Gan, Ruiyan Liu +3 more
A concise preparation of optically active l or d-6-methoxytryptophan ethyl ester 21 was developed via the Fischer indole/Schollkopf protocol from 6-Methoxy-3-methylindole 16 (four steps, 58% overall yield).
Tetrahedron LettersRegiospecific bromination of 3-methylindoles with N-bromosuccinimide
48 Citations1995Puwen Zhang, Ruiyan Liu +1 more