Enantioselective total synthesis of eudistomidins G, H, and I

Tetrahedron

Volumn 68, Issue 31, 2012, Pages 6186-6192

  Ishiyama, Haruaki ^a   Yoshizawa, Kazuaki ^a   Kobayashi, Jun'ichi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Absolute configuration; Eudistoma glaucus; Eudistomidins G, H, and I; Total synthesis

Indexed keywords

5 BROMOTRYPTAMINE; ALKALOID DERIVATIVE; EUDISTOMIDIN G; EUDISTOMIDIN H; EUDISTOMIDIN I; TRYPTAMINE; UNCLASSIFIED DRUG;

AMIDATION; ARTICLE; BISCHLERE NAPIERALSKI REACTION; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CIRCULAR DICHROISM; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; EUDISTOMA GLAUCUS; METHYLATION; NOYORI CATALYTIC ASYMMETRIC HYDROGEN TRANSFER REACTION; POLYMERIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; STEREOCHEMISTRY; UROCHORDATA;

EUDISTOMA; GLAUCUS;

EID: 84862653304     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.05.071     Document Type: Article

References (14)

1. Takahashi, Y.; Ishiyama, H.; Kubota, T.; Kobayashi, J. Bioorg. Med. Chem. Lett. 2010, 20, 4100-4103.
2. Suzuki, T.; Kubota, T.; Kobayashi, J. Bioorg. Med. Chem. Lett. 2011, 21, 4220-4223.
3. Kobayashi, J.; Cheng, J.-F.; Ohta, T.; Nozoe, S.; Ohizumi, Y.; Sasaki, T. J. Org. Chem. 1990, 55, 3666-3670.
4. Ito, T.; Kitajima, M.; Takayama, H. Tetrahedron Lett. 2009, 50, 4506-4508.
5. Mokrosz, M. J.; Paluchowska, M. H.; Misztal, S.; Mkrosz, J. L. Heterocycles 1994, 37, 227-233.
6. (a) Uematsu, N.; Fujii, A.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 4916-4917;
7. 1H NMR coupling constant. Since the stereochemistry at C-10 in 2 was S, the absolute stereochemistry at C-1 was deduced to be R configuration.
8. Bischler, A.; Napieralski, B. Chem. Ber. 1893, 26, 1891e1903.
9. Liu, J.-J.; Hino, T.; Tsuruoka, A.; Harada, N.; Nakagawa, M. J. Chem. Soc., Perkin Trans. 1 2000, 3487-3494.
10. Brogan, J. T.; Stoops, S. L.; Crew, B. C.; Marnett, L. J.; Linsley, C. W. ACS Chem. Neurosci. 2011, 2, 633-639.
11. Freidinger, R. M.; Hinkle, J. S.; Perlow, D. S.; Arison, B. H. J. Org. Chem. 1983, 48, 77-81.
12. Muratore, M. E.; Holloway, C. A.; Pilling, A. W.; Storer, R. I.; Trevitt, G.; Dixon, D. J. J. Am. Chem. Soc. 2009, 131, 10796-10797.
13. Schumacher, R. W.; Davidson, B. S. Tetrahedron 1999, 55, 935-942.
14. 4 provided complex mixture including tryptamine.