Concise synthesis of the (+/-)-Nb-desmethyl-meso-chimonanthine.
@article{Menozzi2006ConciseSO,
title={Concise synthesis of the (+/-)-Nb-desmethyl-meso-chimonanthine.},
author={Candice Marie Menozzi and Peter I Dalko and Janine Cossy},
journal={Chemical communications},
year={2006},
volume={44},
pages={
4638-40
}
}The first total synthesis of the bis-pyrroloindoline alkaloid (+/-)-Nb-desmethyl-meso-chimonanthine, having a pseudo C2-symmetry, was realised in a seven-step convergent sequence without the use of protecting groups.
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References
SHOWING 1-10 OF 23 REFERENCES
Total synthesis of (+/-)-perophoramidine.
- ChemistryJournal of the American Chemical Society
- 2004
The first total synthesis of racemic perophoramidine is described. The key step features the highly stereoselective introduction of the vicinial quaternary centers via base-promoted carbon-carbon…
Enantioselective Construction of Vicinal Stereogenic Quaternary Centers by Dialkylation: Practical Total Syntheses of (+)- and meso-Chimonanthine.
- ChemistryAngewandte Chemie
- 2000
A rare example of high diastereoselectivity arising from the combination of a prostereogenic enolate with a chiral electrophile containing a sp(3) carbon atom is the key feature of the asymmetric synthesis of the C(2) stereoisomer.
Asymmetric Synthesis of (−)-Trichodiene. Generation of Vicinal Stereogenic Quaternary Centers via the Thio-Claisen Rearrangement
- Chemistry
- 1998
The use of chiral bicyclic lactams, in their thiocarbonyl form 9, has been shown to serve as important intermediates for producing α-quaternary alkyl derivatives 8, which were readily transformed…
Stereoselective generation of vicinal stereogenic quaternary centers by photocycloaddition of 5-methoxy oxazoles to alpha-keto esters: synthesis of erythro beta-hydroxy dimethyl aspartates.
- ChemistryOrganic & biomolecular chemistry
- 2004
The photocycloaddition of methyl pyruvate and methyl phenylglyoxylate, respectively, to 5-methoxy oxazoles bearing additional substituents at C-2 and C-4 leads to bicyclic oxetanes 2 and 3 with high…
Catalytic enantioselective construction of all-carbon quaternary stereocenters
- Chemistry
- 2006
Catalytic enantioselective construction of all-carbon quaternary stereocenters, i.e. carbon atoms bearing four different carbon substituents, poses a particular challenge in organic synthesis. This…