Total synthesis of nafuredin-γ, a γ-lactone related to nafuredin with selective inhibitory activity against NADH-fumarate reductase

Tetrahedron Letters

Volumn 44, Issue 34, 2003, Pages 6441-6444

  Nagamitsu, Tohru ^a   Takano, Daisuke ^a   Shiomi, Kazuro ^a   Ui, Hideaki ^a   Yamaguchi, Yuichi ^a   Masuma, Rokuro ^a   Harigaya, Yoshihiro ^a   Kuwajima, Isao ^a,b   Omura, Satoshi ^a  

^a KITASATO UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FUMARATE REDUCTASE; GAMMA LACTONE DERIVATIVE; GAMMA NAFUREDIN; NICOTINAMIDE ADENINE DINUCLEOTIDE NUCLEOSIDASE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; ENZYME INHIBITION; INFRARED SPECTROMETRY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0042698439     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01583-1     Document Type: Article

References (27)

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27. 3) enol δ 0.86 (t, 3H, J=7.6 Hz, H-18), 0.97 (d, 3H, J=6.7 Hz, 10-Me), 0.99 (d, 3H, J=6.6 Hz, 16-Me), 1.32 (m, 2H, H-17), 1.46 (s, 3H, 4-Me), 1.70 (s, 3H, 12-Me), 1.91-2.12 (m, 3H, H-11 and H-16), 2.36-2.43 (m, 1H, H-10), 4.25 (d, 1H, J=7.3 Hz, H-5), 5.46 (dd, 1H, J=14.8, 7.6 Hz, H-15), 5.50 (dd, 1H, J=15.5, 7.3 Hz, H-6), 5.70 (dd, 1H, J=15.5, 7.3 Hz, H-9), 5.76 (d, 1H, J=10.9 Hz, H-13), 6.00 (dd, 1H, J=15.5, 10.2 Hz, H-8), 6.15 (s, 1H, H-3), 6.18 (dd, 1H, J=14.8, 10.9 Hz, H-14), 6.30 (dd, 1H, J=15.5, 10.2 Hz, H-7), ketone δ 0.86 (t, 3H, J=7.6 Hz, H-18), 0.97 (d, 3H, J=6.7 Hz, 10-Me), 0.99 (d, 3H, J=6.6 Hz, 16-Me), 1.32 (m, 2H, H-17), 1.54 (s, 3H, 4-Me), 1.70 (s, 3H, 12-Me), 1.91-2.12 (m, 3H, H-11 and H-16), 2.32 (d, 1H, J=18.8 Hz, 1/2 H-3), 2.36-2.43 (m, 1H, H-10), 3.03 (d, 1H, J=18.8 Hz, 1/2 H-3), 4.21 (m, 1H, H-5), 5.46 (dd, 1H, J=14.8, 7.6 Hz, H-15), 5.50 (dd, 1H, J=15.5, 7.3 Hz, H-6), 5.70 (dd, 1H, J=15.5, 7.3 Hz, H-9), 5.76 (d, 1H, J=10.9 Hz, H-13), 6.00 (dd, 1H, J=15.5, 10.2 Hz, H-8), 6.18 (dd, 1H, J=14.8, 10.9 Hz, H-14), 6.30 (dd, 1H, J=15.5, 10.2 Hz, H-7).