Asymmetric synthesis of (+)-L-733, 060 and (+)-CP-99, 994 based on a new chiral 3-piperidinol synthon.

@article{Huang2003AsymmetricSO,
  title={Asymmetric synthesis of (+)-L-733, 060 and (+)-CP-99, 994 based on a new chiral 3-piperidinol synthon.},
  author={P. Huang and Liang Liu and Bang-Guo Wei and Yuan-Ping Ruan},
  journal={Organic letters},
  year={2003},
  volume={5 11},
  pages={
          1927-9
        }
}
[reaction: see text] Selective and potent neurokinin substance P receptor antagonists (+)-L-733, 060 (1) and (+)-CP-99, 994 (2) have been synthesized starting from a new (3S)-piperidinol synthon derived from l-glutamic acid. The methods featured a C-2 regioselective reduction of glutarimide (9), Lewis acid-promoted Si to C-2 phenyl group migration of 10, and stereoselective reduction of acetylated oxime 19 as the key steps. 
A stereoselective synthesis of (+)-L-733,060 from ethyl (R)-(+)-2,3-epoxypropanoate
An asymmetric synthesis of neurokinin substance P receptor antagonist (+)-L-733,060 starting from enantiomerically pure ethyl (R)-(+)-2,3-epoxypropanoate (ethyl glycidate) is described. The synthesisExpand
Synthesis of (+)-L-733,060, (+)-CP-99,994 and (2S,3R)-3-hydroxypipecolic acid: application of an organocatalytic direct vinylogous aldol reaction.
The γ-butenolide obtained from an organocatalyzed, direct vinylogous aldol reaction of γ-crotonolactone and benzaldehyde serves as the key starting material in the expedient synthesis of aExpand
A concise enantioselective synthesis of l-(−)-733,061 and (2S,3S)-methyl 3-aminopiperidine-2-carboxylate using catalytic enantioselective aza-Henry reaction as key step
Abstract An efficient enantioselective synthesis of l -(−)-733,061 and (2S,3S)-methyl 3-aminopiperidine-2-carboxylate is accomplished by means of catalytic enantioselective aza-Henry reaction. A keyExpand
A versatile approach for the asymmetric syntheses of (1R,9aR)-epiquinamide and (1R,9aR)-homopumiliotoxin 223G.
TLDR
A key feature of this approach is the flexible introduction of a functionalized C(4) side chain to (S)-3-benzyloxyglutarimide 7 in a regio- and diastereoselective manner that could be useful for the syntheses of 8-dehydrodesmethylpumiliotoxins such as alkaloid 235C. Expand
A short enantioselective synthesis of (+)-L-733,060 via Shi epoxidation of a homoallylic carboxylate
Abstract A short and efficient enantioselective synthesis of (+)-L-733,060 in 92% ee via Shi epoxidation of a homoallylic carboxylate is described. Johnson–Claisen rearrangement was employed toExpand
Stereoselective approach to cis-2,3-disubstituted piperidines via reduction of N-acyliminium ion intermediate: enantioselective synthesis of (+)-(2S,3S)-CP-99,994.
TLDR
A very simple and efficient stereoselective approach to cis-2,3-disubstituted piperidines via the reduction of N-acyliminium ion intermediates is described, exemplified by the enantioselectives total synthesis of (+)-(2S,3S)-CP-99,994. Expand
alpha-Amino 1,3-Dithioketal Mediated Asymmetric Synthesis of Piperidines (L-733,060) and Tetrahydrofuran Glycines.
Sulfinimine-derived alpha-amino 1,3-dithianes, alpha-amino carbonyl chiral building blocks, are utilized in asymmetric syntheses of (+)-(tetrahydrofuran-2-yl)glycine and the 2,3-disubstitutedExpand
Syntheses of enantio-enriched chiral building blocks from L-glutamic acid
Abstract Starting from lactone-amide 8, easily derived from l -glutamic acid, enantioselective syntheses of (S)-tetrahydrofuran 2-carboxamide derivative 2 and a protected (S)-3-hydroxypiperidin-2-oneExpand
An enantioselective synthesis of (+)-azimic acid
Herein we report a concise enantioselective synthesis of (+)-azimic acid starting from (5S,6S)-6-methyl-5-benzyloxy-2-piperidinone 8a, which was prepared from protected (S)-3-hydroxyglutarimide 6Expand
A divergent approach for asymmetric syntheses of (+)-spicigerine, (+)-cassine and their 3-epimers
Abstract An efficient approach for asymmetric synthesis of (+)-spicigerine, (+)-cassine and their 3-epimers has been developed through the intramolecular diastereoselective tandemExpand
...
1
2
3
4
5
...

References

SHOWING 1-10 OF 24 REFERENCES
A New Approach for Asymmetric Synthesis of (R)-3-Methylpyrrolidine Alkaloids from (S)-Malic Acid
TLDR
Two, three-step reductive de-hydroxylation procedures afforded dimethyl (R)-2-methylsuccinate 11, which was further transformed into the natural enantiomers of the ant venom alkaloids (R-leptothoracine 1 and (R)3-methyl-N-(2-phenylethyl)-pyrrolidine 2. Expand
Asymmetric synthesis of (2S,3S)-3-hydroxy-2-phenylpiperidine via ring expansion
Abstract A catalytic highly enantioselective (99% ee) preparation of N - tert -butyloxycarbonyl-(2 S ,3 S )-3-hydroxy-2-phenyl-piperidine and N - tert -butyloxycarbonyl-(2 SExpand
A New Approach to (−)-Anisomycin
Abstract (R)-(−)-1-Benzyloxycarbonyl-2-(4-methoxyphenyl)methyl-3-pyrroline (16) was prepared from (S)-malic acid. The key steps involved a highly regio and trans stereoselective reductive alkylationExpand
An easy access to protected (4S, 5R)-5-Alkyl-4-hydroxy-2-pyrrolidinones and their use as versatile synthetic intermediates
Abstract A versatile approach to enantiopure (4S, 5R)-5-alkyl-4-hydroxy-2-pyrrolidinones is described. The key steps involve a regioselective Grignard reagent addition to (S)-malimides, andExpand
Asymmetric synthesis of (−)-(R)-pyrrolam A starting from (S)-malic acid
An asymmetric synthesis of natural (−)-pyrrolam A starting from natural (S)-malic acid is described. The stereogenic center was established via a highly trans-diastereoselective reductive alkylationExpand
Stereoselective synthesis of (+)-CP-99,994: A substance P non-peptide antagonist
Abstract A highly stereoflexible total synthesis of (+)-CP-99,994 is achieved starting, from (S)-serine, key steps being a diastereoselective Grignard addition, a one-pot reductive protection of anExpand
STEREOSELECTIVE SYNTHESIS OF (2S, 3S)-3-HYDROXY-2-PHENYLPIPERIDINES, PRECURSORS OF NON-PEPTIDIC SUBSTANCE P ANTAGONISTS
(2S)-N-Boc-3-oxo-2-phenylpiperidine 5 and (2S,3S)-N-Boc-3-hydroxy-2-phenylpiperidine 6, known chiral building blocks for the synthesis of non-peptidic substance P antagonists, were prepared fromExpand
First asymmetric synthesis of (2R, 3R)-3-amino-1-benzyl-2-methyl-pyrrolidine via a highly diastereoselective reductive alkylation
Abstract The first asymmetric synthesis of (2R, 3R)-3-amino-1-benzyl-2-methylpyrrolidine, the parent diamine of antipsychotic agent, emonapride, from (S)-malic acid was achieved via a highlyExpand
A new approach to (S)-4-hydroxy-2-pyrrolidinone and its 3-substituted analogues
Abstract Successive treatment of a phenyl thioether derived from ( S )-malic acid with n- BuLi, lithium naphthalenide (LN), and electrophiles led to 4-hydroxy-3-substituted 2-pyrrolidinones inExpand
Enantioselective synthesis of NK-1 receptor antagonists (+)-CP-99,994 and (+)-CP-122,721
An enantioselective total synthesis of NK-1 receptor antagonists, (+)-CP-99,994 and (+)-CP-122,721, is described. The key steps are diastereoselective addition of vinyllithium to a chiralExpand
...
1
2
3
...