The quest for quinine: those who won the battles and those who won the war.

@article{Kaufman2005TheQF,
  title={The quest for quinine: those who won the battles and those who won the war.},
  author={Teodoro S. Kaufman and Edmundo A. R{\'u}veda},
  journal={Angewandte Chemie},
  year={2005},
  volume={44 6},
  pages={
          854-85
        }
}
For a long time, the synthesis of quinine constituted an elusive target. In 2004, which marked the 60th anniversary of the publication of the approach used by Woodward and Doering to synthesize quinine, two new stereocontrolled total syntheses of the natural product were accomplished. Together with the well-publicized first stereocontrolled total synthesis of quinine by Stork in 2001, these publications evidence the revival of interest of organic chemists in the synthesis of this compound, once… Expand
Asymmetric Synthesis of Quinine: A Landmark in Organic Synthesis
Ever since its isolation in 1820, Quinine has played a crucial role in the development of organic chemistry, the chemical industry and modern medicine. A total synthesis of quinine, widely regardedExpand
Rabe rest in peace: confirmation of the rabe-kindler conversion of D-quinotoxine into quinine: experimental affirmation of the Woodward-Doering formal total synthesis of quinine.
Robert Burns Woodward and William von Eggers Doering of Harvard University published a communication in 1944 and a full paper in 1945 in the Journal of the American Chemical Society both entitledExpand
The Woodward-Doering/Rabe-Kindler total synthesis of quinine: setting the record straight.
TLDR
A detailed examination of the synthesis of cinchona alkaloids is presented, and previously unpublished material combined with unpublished material and numerous interviews give insight into the lives of the personalities in this nearly 100-year saga. Expand
4-IODO-6-METHOXYQUINOLINE
As part of a project directed towards establishing a fully stereocontrolled total synthesis of the anti-malarial agent quinine] we required access to the title compound (6) . The only reportedExpand
Natural Products That Changed Society
TLDR
Until the end of the 19th century all drugs were natural products or minerals, but during the 20th and the 21st century synthetic compounds became the major source of drugs. Expand
Indole Alkaloid Synthesis Facilitated by Photoredox Catalytic Radical Cascade Reactions.
TLDR
The visible-light-driven cascade strategy will find further utility in the realm of natural product synthesis, and expansion of this catalytic, scalable, and general methodology permitted the total synthesis of a large collection of indole alkaloids. Expand
Organocatalysis: Cinchona catalysts
The resurgence of asymmetric organocatalysis has been accompanied by the development of countless synthetic methodologies making use of Cinchona alkaloids (or their derivatives) as catalysts.Expand
Isolation, Synthesis, and Biological Activity of Quindoline, a Valuable­ Indoloquinoline Natural Product and Useful Key Intermediate­
Quindoline is one of the simplest naturally occurring monomeric indoloquinoline alkaloids. Chemists exhibited interest in this compound before it was isolated from a natural source. The differentExpand
Crystal structure of quinine: the effects of vinyl and methoxy groups on molecular assemblies of Cinchona alkaloids cannot be ignored.
TLDR
Hierarchical comparison on the crystal structures of a series of Cinchona alkaloids including quinine clearly demonstrated that only small structural differences of a molecule, particularly the position of the vinyl group, cause a significant variety of assembly manner in the crystalline state. Expand
Organic Chemistry: An Indian Journal
The quinuclidine ring is used in synthesis of various therapeutically important molecules and also important intermediate and synthesis of some drugs like azasetron, benzoclidine, palonosetron,Expand
...
1
2
3
4
5
...

References

SHOWING 1-10 OF 270 REFERENCES
Recent advances in the chemistry of natural products
  • R. Woodward
  • Chemistry, Medicine
  • Pure and applied chemistry. Chimie pure et appliquee
  • 1968
TLDR
The structure of the vitamin B12 molecule, revealed to us by the beautiful x-ray crystallographic studies of Dorothy Hodgkin, exhibits certain resemblances to other natural substances, and the principle of orbital symmetry conservation arose directly from studies on vitamin B 12 synthesis. Expand
Some contributions to regio and stereo control: From cincholoipon and cantharidin to the present
  • G. Stork
  • Chemistry, Medicine
  • Medicinal research reviews
  • 1999
A condensed review of some of the major original contributions of the author's research group to organic synthesis during more than half a century. The emphasis is on methodology, especially as itExpand
Total Synthesis of Taxol. 1. Retrosynthesis, Degradation, and Reconstitution
A successful strategy for the enantioselective synthesis of the natural stereoisomer of Taxol (1) has been developed. This strategy utilized the convergent assembly of Taxol's central eight-memberedExpand
Enantioselective synthesis of (−)-meroquinene through tandem Michael reaction methodology.
Abstract An enantioselective approach to the synthesis of non natural (−)-meroquinene 1 based on sequential inter- and intramolecular Michael reaction between (L)-menthylExpand
The total synthesis of vitamin B12
  • R. Woodward
  • Chemistry, Medicine
  • Pure and applied chemistry. Chimie pure et appliquee
  • 1973
TLDR
It was particularly appropriate, I think, and most pleasant for us this morning to see the splendid film provided by the authors' Russian friends, in which the very successful Symposium at Riga was enshrined for posterity. Expand
Large-Scale Synthesis of the Anti-Cancer Marine Natural Product (+)-Discodermolide. Part 5: Linkage of Fragments C1-6 and C7-24 and Finale
The finale of the large-scale preparation of 60 g of the highly complex marine natural product, (+)-discodermolide (1), using a hybridized Novartis−Smith−Paterson synthetic route is presented. ThisExpand
Total synthesis of taxol
TLDR
The total synthesis of taxol is reported by a convergent strategy, which opens a chemical pathway for the production of both the natural product itself and a variety of designed taxoids. Expand
Total synthesis and structural revision of (+)-amphidinolide W.
TLDR
An enantioselective first total syntheis of amphidinolide W and a revision of its C6 absolute stereochemistry are described, which have shown potent antitumor properties against a variety of NCI tumor cell lines. Expand
The Synthesis of Ethyl 5-Vinyl-2-Quinuclidine Carboxylate
Abstract The synthesis of the minor indolic cinchona alkaloid, cinchonexine (1), from ethyl-5-vinyl-2-quinuclidine carboxylate (2) was reported in 19581 but the preparation of 2 was not describedExpand
The total synthesis of chlorophyll a
The total synthesis of chlorophyll a starting from Knorr's pyrrole (1) is described with full experimental detail. Forty six stages are involved to reach the target molecule, chlorin e6 trimethylExpand
...
1
2
3
4
5
...