The first total synthesis of (±)-terpestacin, HIV syncytium formation inhibitor

Tetrahedron Letters

Volumn 39, Issue 1-2, 1998, Pages 83-86

  Tatsuta, Kuniaki ^a   Masuda, Naoyuki ^a   Nishida, Hidemitsu ^a  

^a WASEDA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; SESTERTERPENE; TERPESTACIN; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR OVERHAUSER EFFECT; REACTION ANALYSIS;

EID: 0031973847     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10494-4     Document Type: Article

References (11)

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6. 3 (270, 400 and 500 MHz, δ; TMS=0) are the following. 1: δ 0.98 (3H,s), 1.28 (3H,d,7.2Hz), 4.04(1H, dd, J=3.0&10.0 Hz), 5.12 (1H, m), 5.23 (1H, m), 5.39 (1H, m). 3: δ 2.35 (1H, dd, 2.2&18.6Hz), 2.87 (1H, dd, J= 10.3&18.6Hz), 4.46 (1H, d, J=4.3Hz), 5.24 (1H, d, J= 6.1Hz). 4: δ 0.10 (6H, s), 0.85 (9H, s), 1.31 (3H, d, J=7.7Hz), 4.25 (1H, br t, J=3.0Hz). 5: δ 4.26 (1H, d, J = 13.8Hz), 4.32 (1H, d, J=8.3 Hz), 4.57 (1H, d, J=13.8Hz), 4.83 (1H, s), 7.20-7.35 (5H, m). 6: δ 3.80 (3H, s), 4.65 (1H, d, J=6.0Hz), 8.33 (1H, d, J=3.2Hz). 7a: δ 4.94 (1H, d, J=8.0Hz), 5.00 (1H, dd, J=2.4&10.4Hz), 5.10 (1H, dd, J=2.4&7.4Hz), 5.73 (1H, ddd, J=7.4&8.0&10.4Hz), 10.22 (1H, br s). 8: δ 1.04 (3H, d, J = 6.8Hz), 2.08 (1H, ddd, J=2.8&3.2&10.0Hz), 2.27 (1H, m, 6.8Hz), 3.51 (1H, br d, J=8.0Hz), 4.86 (1H, d, J=2.0Hz), 4.94 (1H, br d, J=10.0Hz). 9: δ 4.20-4.35 (1H, m), 4.28 (1H, d, J=2.0Hz), 4.45-4.53 (1H, m), 4.99 (1H, dd, J=2.0&8.4Hz). 10: δ 2.47 (2H, dt, J=3.6&8.4Hz), 4.16 (2H, d, J=6.8Hz), 5.12 (1H, dt, J=1.2&7.0Hz), 5.27 (1H, dt, J=1.2&6.8 Hz), 9.72 (1H, t, J=3.6Hz). 11: δ 1.30 (6H, t, J= 6.8Hz), 2.02 (3H, s), 3.99-4.15 (4H, m, J=6.8 Hz), 4.98-5.10 (2H, m, J=6.0Hz), 5.26 (1H, t, J= 6.0Hz). 12: δ 4.10 (2H, d, J=7.0Hz), 5.10 (1H, t, J=6.8 Hz), 5.19 (1H, ddd, J=4.4&10.0&13.0 Hz), 5.44 (1H, dt, J=1.6& 7.0Hz). 13: δ 1.07 (3H, d, J= 7.0Hz), 2.05 (3H, s), 4.79 (1H, s), 4.96 (1H, t, J=7.6Hz), 5.03 (1H, t, J=6.4Hz), 5.19 (1H, ddd, J=4.0&10.0& 18.0Hz). 14: δ 3.49 (3H, s), 4.19-4.30 (3H, J=6.0Hz), 4.55 (1H, dd, J=6.0&8.0Hz), 4.84 (1H, d, J=6.6Hz), 4.96 (1H, d, J=6.6 Hz). 15: δ 3.24 (1H, dq, J=7.2&25.4Hz), 3.64 (3H, s), 9.75 (1H, dd, J=1.4&3.4Hz). 16: δ 4.92 (1H, t, J=6.0 Hz), 5.34 (1H, t, J=6.2Hz), 6.60 (1H, t, J=8.0 Hz). 17: δ -0.06 (3H, s), 0.00 (3H, s), 0.86 (9H, s), 3.54 (2H, br d, J = 4.4Hz), 3.85 (1H, dd, J=3.8&10.6Hz), 5.48 (1H, t, J=6.4Hz). 18: δ 0.85 (3H, s), 3.66 (1H, d, J=5.0Hz), 3.81 (1H, dd, J=4.0&10.2Hz). 19(α): δ 3.43 (3H, s), 3.96 (1H, 3.6&10.4Hz). (β): δ 3.36 (3H, s), 3.89 (1H, dd, J=3.6& 10.4Hz). 20: δ 4.09 (1H, dd, J=7.4&11.0Hz), 4.57 (1H, dd, J=3.2&11.0Hz), 5.30 (1H, dd, J=4.0&12.2Hz).
7. Mander L.N., Sethi S.P. Tetrahedron Lett. 24:1983;5425-5428.
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9. The configurations at the C1 and C2 remain undetermined.
10. Blanchette M.A., Choy W., Davis J.T., Essenfeld A.P., Masamune S., Roush W.R., Sakai T. Tetrahedron Lett. 25:1984;2183-2186.
11. An authentic sample of terpestacin was kindly provided by Prof. T. Oki, Toyama Prefectural University.