共 52 条
Synthetic Studies toward the C14-C29 Fragment of Mirabalin
被引:14
作者:

Cornil, Johan
论文数: 0 引用数: 0
h-index: 0
机构:
PSL Res Univ, ESPCI Paris, CNRS,UMR 8231, Lab Chim Organ,Inst Chem Biol & Innovat CBI, 10 Rue Vauquelin, F-75231 Paris 05, France PSL Res Univ, ESPCI Paris, CNRS,UMR 8231, Lab Chim Organ,Inst Chem Biol & Innovat CBI, 10 Rue Vauquelin, F-75231 Paris 05, France

Echeverria, Pierre-Georges
论文数: 0 引用数: 0
h-index: 0
机构:
PSL Res Univ, Chim ParisTech, CNRS, Inst Rech Chim Paris, F-75005 Paris, France PSL Res Univ, ESPCI Paris, CNRS,UMR 8231, Lab Chim Organ,Inst Chem Biol & Innovat CBI, 10 Rue Vauquelin, F-75231 Paris 05, France

Reymond, Sebastien
论文数: 0 引用数: 0
h-index: 0
机构:
PSL Res Univ, ESPCI Paris, CNRS,UMR 8231, Lab Chim Organ,Inst Chem Biol & Innovat CBI, 10 Rue Vauquelin, F-75231 Paris 05, France PSL Res Univ, ESPCI Paris, CNRS,UMR 8231, Lab Chim Organ,Inst Chem Biol & Innovat CBI, 10 Rue Vauquelin, F-75231 Paris 05, France

Phansavath, Phannarath
论文数: 0 引用数: 0
h-index: 0
机构:
PSL Res Univ, Chim ParisTech, CNRS, Inst Rech Chim Paris, F-75005 Paris, France PSL Res Univ, ESPCI Paris, CNRS,UMR 8231, Lab Chim Organ,Inst Chem Biol & Innovat CBI, 10 Rue Vauquelin, F-75231 Paris 05, France

Ratovelomanana-Vidal, Virginie
论文数: 0 引用数: 0
h-index: 0
机构:
PSL Res Univ, Chim ParisTech, CNRS, Inst Rech Chim Paris, F-75005 Paris, France PSL Res Univ, ESPCI Paris, CNRS,UMR 8231, Lab Chim Organ,Inst Chem Biol & Innovat CBI, 10 Rue Vauquelin, F-75231 Paris 05, France

Guerinot, Amandine
论文数: 0 引用数: 0
h-index: 0
机构:
PSL Res Univ, ESPCI Paris, CNRS,UMR 8231, Lab Chim Organ,Inst Chem Biol & Innovat CBI, 10 Rue Vauquelin, F-75231 Paris 05, France PSL Res Univ, ESPCI Paris, CNRS,UMR 8231, Lab Chim Organ,Inst Chem Biol & Innovat CBI, 10 Rue Vauquelin, F-75231 Paris 05, France

Cossy, Janine
论文数: 0 引用数: 0
h-index: 0
机构:
PSL Res Univ, ESPCI Paris, CNRS,UMR 8231, Lab Chim Organ,Inst Chem Biol & Innovat CBI, 10 Rue Vauquelin, F-75231 Paris 05, France PSL Res Univ, ESPCI Paris, CNRS,UMR 8231, Lab Chim Organ,Inst Chem Biol & Innovat CBI, 10 Rue Vauquelin, F-75231 Paris 05, France
机构:
[1] PSL Res Univ, ESPCI Paris, CNRS,UMR 8231, Lab Chim Organ,Inst Chem Biol & Innovat CBI, 10 Rue Vauquelin, F-75231 Paris 05, France
[2] PSL Res Univ, Chim ParisTech, CNRS, Inst Rech Chim Paris, F-75005 Paris, France
关键词:
POTENT CYTOTOXIC MACROLIDE;
FORMAL TOTAL SYNTHESIS;
SWINHOLIDE-A;
ABSOLUTE STEREOSTRUCTURE;
DIMERIC MACROLIDE;
SUPERSTOLIDE-A;
RIFAMYCIN-S;
SPONGE;
STRATEGY;
SUBUNITS;
D O I:
10.1021/acs.orglett.6b02162
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
A convergent synthesis of one isomer of the C14-C29 fragment of mirabalin is disclosed. The key steps include a Marshall allenylation, a Mukaiyama aldol reaction and a Crimmins aldolization, which allow the control of 10 out of 25 stereogenic centers present in the molecule.
引用
收藏
页码:4534 / 4537
页数:4
相关论文
共 52 条
- [1] Stereochemistry of nucleophilic substitution reactions depending upon substituent: Evidence for electrostatic stabilization of pseudoaxial conformers of oxocarbenium ions by heteroatom substituents[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (50) : 15521 - 15528Ayala, L论文数: 0 引用数: 0 h-index: 0机构: Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USALucero, CG论文数: 0 引用数: 0 h-index: 0机构: Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USARomero, JAC论文数: 0 引用数: 0 h-index: 0机构: Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USATabacco, SA论文数: 0 引用数: 0 h-index: 0机构: Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USAWoerpel, KA论文数: 0 引用数: 0 h-index: 0机构: Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA
- [2] Iron-catalyzed cross-coupling between C-bromo mannopyranoside derivatives and a vinyl Grignard reagent: toward the synthesis of the C31-C52 fragment of amphidinol 3[J]. TETRAHEDRON, 2013, 69 (36) : 7759 - 7770Bensoussan, Charlelie论文数: 0 引用数: 0 h-index: 0机构: ESPCI ParisTech, Chim Organ Lab, CNRS, UMR 7084, F-75231 Paris 05, France ESPCI ParisTech, Chim Organ Lab, CNRS, UMR 7084, F-75231 Paris 05, FranceRival, Nicolas论文数: 0 引用数: 0 h-index: 0机构: Univ Strasbourg ECPM, CNRS, UMR 7509, Lab Synth & Catalyse Asymetr, F-67087 Strasbourg 02, France ESPCI ParisTech, Chim Organ Lab, CNRS, UMR 7084, F-75231 Paris 05, FranceHanquet, Gilles论文数: 0 引用数: 0 h-index: 0机构: Univ Strasbourg ECPM, CNRS, UMR 7509, Lab Synth & Catalyse Asymetr, F-67087 Strasbourg 02, France ESPCI ParisTech, Chim Organ Lab, CNRS, UMR 7084, F-75231 Paris 05, FranceColobert, Francoise论文数: 0 引用数: 0 h-index: 0机构: Univ Strasbourg ECPM, CNRS, UMR 7509, Lab Synth & Catalyse Asymetr, F-67087 Strasbourg 02, France ESPCI ParisTech, Chim Organ Lab, CNRS, UMR 7084, F-75231 Paris 05, FranceReymond, Sebastien论文数: 0 引用数: 0 h-index: 0机构: ESPCI ParisTech, Chim Organ Lab, CNRS, UMR 7084, F-75231 Paris 05, France ESPCI ParisTech, Chim Organ Lab, CNRS, UMR 7084, F-75231 Paris 05, FranceCossy, Janine论文数: 0 引用数: 0 h-index: 0机构: ESPCI ParisTech, Chim Organ Lab, CNRS, UMR 7084, F-75231 Paris 05, France ESPCI ParisTech, Chim Organ Lab, CNRS, UMR 7084, F-75231 Paris 05, France
- [3] Synthesis of 8-Desmethoxy Psymberin: A Putative Biosynthetic Intermediate Towards the Marine Polyketide Psymberin[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (25) : 8300 - 8308Bielitza, Max论文数: 0 引用数: 0 h-index: 0机构: Univ Dusseldorf, Inst Bioorgan Chem, Forschungszentrum Julich, D-52426 Julich, Germany Univ Dusseldorf, Inst Bioorgan Chem, Forschungszentrum Julich, D-52426 Julich, GermanyPietruszka, Joerg论文数: 0 引用数: 0 h-index: 0机构: Univ Dusseldorf, Inst Bioorgan Chem, Forschungszentrum Julich, D-52426 Julich, Germany Univ Dusseldorf, Inst Bioorgan Chem, Forschungszentrum Julich, D-52426 Julich, Germany
- [4] Total synthesis of (+)-strictifolione[J]. ORGANIC LETTERS, 2003, 5 (11) : 1995 - 1997BouzBouz, S论文数: 0 引用数: 0 h-index: 0机构: Ecole Super Phys & Chim Ind Ville Paris, CNRS, Chim Organ Lab, F-75231 Paris 05, France Ecole Super Phys & Chim Ind Ville Paris, CNRS, Chim Organ Lab, F-75231 Paris 05, FranceCossy, J论文数: 0 引用数: 0 h-index: 0机构: Ecole Super Phys & Chim Ind Ville Paris, CNRS, Chim Organ Lab, F-75231 Paris 05, France Ecole Super Phys & Chim Ind Ville Paris, CNRS, Chim Organ Lab, F-75231 Paris 05, France
- [5] Efficient strategy for the synthesis of stereopentad subunits of scytophycin, rifamycin S, and discodermolide[J]. ORGANIC LETTERS, 2001, 3 (25) : 3995 - 3998BouzBouz, S论文数: 0 引用数: 0 h-index: 0机构: Ecole Super Phys & Chim Ind Ville Paris, CNRS, Lab Chim Organ, F-75231 Paris 05, France Ecole Super Phys & Chim Ind Ville Paris, CNRS, Lab Chim Organ, F-75231 Paris 05, FranceCossy, J论文数: 0 引用数: 0 h-index: 0机构: Ecole Super Phys & Chim Ind Ville Paris, CNRS, Lab Chim Organ, F-75231 Paris 05, France Ecole Super Phys & Chim Ind Ville Paris, CNRS, Lab Chim Organ, F-75231 Paris 05, France
- [6] STRUCTURE OF SWINHOLIDE-A, A NEW MACROLIDE FROM THE MARINE SPONGE THEONELLA-SWINHOEI[J]. TETRAHEDRON LETTERS, 1985, 26 (04) : 511 - 514CARMELY, S论文数: 0 引用数: 0 h-index: 0KASHMAN, Y论文数: 0 引用数: 0 h-index: 0
- [7] 1,3-SYN DIASTEREOSELECTIVE REDUCTION OF BETA-HYDROXYKETONES UTILIZING ALKOXYDIALKYLBORANES[J]. TETRAHEDRON LETTERS, 1987, 28 (02) : 155 - 158CHEN, KM论文数: 0 引用数: 0 h-index: 0机构: SANDOZ RES INST, E HANOVER, NJ 07936 USA SANDOZ RES INST, E HANOVER, NJ 07936 USAHARDTMANN, GE论文数: 0 引用数: 0 h-index: 0机构: SANDOZ RES INST, E HANOVER, NJ 07936 USA SANDOZ RES INST, E HANOVER, NJ 07936 USAPRASAD, K论文数: 0 引用数: 0 h-index: 0机构: SANDOZ RES INST, E HANOVER, NJ 07936 USA SANDOZ RES INST, E HANOVER, NJ 07936 USAREPIC, O论文数: 0 引用数: 0 h-index: 0机构: SANDOZ RES INST, E HANOVER, NJ 07936 USA SANDOZ RES INST, E HANOVER, NJ 07936 USASHAPIRO, MJ论文数: 0 引用数: 0 h-index: 0机构: SANDOZ RES INST, E HANOVER, NJ 07936 USA SANDOZ RES INST, E HANOVER, NJ 07936 USA
- [8] Asymmetric aldol additions with titanium enolates of acyloxazolidinethiones: Dependence of selectivity on amine base and Lewis acid stoichiometry[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (33) : 7883 - 7884Crimmins, MT论文数: 0 引用数: 0 h-index: 0机构: Venable and Kenan Lab. of Chemistry, University of North Carolina, Chapel HillKing, BW论文数: 0 引用数: 0 h-index: 0机构: Venable and Kenan Lab. of Chemistry, University of North Carolina, Chapel HillTabet, EA论文数: 0 引用数: 0 h-index: 0机构: Venable and Kenan Lab. of Chemistry, University of North Carolina, Chapel Hill
- [9] A convenient and chemoselective one-pot oxidation/Wittig reaction for the C2-homologation of carbohydrate-derived glycols[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (24) : 10099 - 10101Crisóstomo, FRP论文数: 0 引用数: 0 h-index: 0机构: Univ La Laguna, Inst Univ Bioorgan Antonio Gonzalez, E-38206 Tenerife, Islas Canarias, SpainCarrillo, R论文数: 0 引用数: 0 h-index: 0机构: Univ La Laguna, Inst Univ Bioorgan Antonio Gonzalez, E-38206 Tenerife, Islas Canarias, SpainMartín, T论文数: 0 引用数: 0 h-index: 0机构: Univ La Laguna, Inst Univ Bioorgan Antonio Gonzalez, E-38206 Tenerife, Islas Canarias, SpainGarcía-Tellado, F论文数: 0 引用数: 0 h-index: 0机构: Univ La Laguna, Inst Univ Bioorgan Antonio Gonzalez, E-38206 Tenerife, Islas Canarias, SpainMartín, VS论文数: 0 引用数: 0 h-index: 0机构: Univ La Laguna, Inst Univ Bioorgan Antonio Gonzalez, E-38206 Tenerife, Islas Canarias, Spain
- [10] SUPERSTOLIDE-A - A POTENT CYTOTOXIC MACROLIDE OF A NEW-TYPE FROM THE NEW-CALEDONIAN DEEP-WATER MARINE SPONGE NEOSIPHONIA-SUPERSTES[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (15) : 6658 - 6663DAURIA, MV论文数: 0 引用数: 0 h-index: 0机构: UNIV NAPLES FEDERICO II,DIPARTIMENTO CHIM SOSTANZE NAT,I-80131 NAPLES,ITALYDEBITUS, C论文数: 0 引用数: 0 h-index: 0机构: UNIV NAPLES FEDERICO II,DIPARTIMENTO CHIM SOSTANZE NAT,I-80131 NAPLES,ITALYPALOMA, LG论文数: 0 引用数: 0 h-index: 0机构: UNIV NAPLES FEDERICO II,DIPARTIMENTO CHIM SOSTANZE NAT,I-80131 NAPLES,ITALYMINALE, L论文数: 0 引用数: 0 h-index: 0机构: UNIV NAPLES FEDERICO II,DIPARTIMENTO CHIM SOSTANZE NAT,I-80131 NAPLES,ITALY论文数: 引用数: h-index:机构: