Type II intramolecular annulations between vinylcarbenoids and furans

Tetrahedron Letters

Volumn 38, Issue 10, 1997, Pages 1737-1740

  Davies, Huw M L ^a   Calvo, Rebecca ^a   Ahmed, Gulzar ^a  

^a UNIVERSITY AT BUFFALO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE; TERPENE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031562485     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00204-9     Document Type: Article

References (9)

1. 1. Isolation and structure determination: (a) Dabrah, T. T.; Harwood, Jr., J.: Huang, L. H.; Jankovich, N. D.; Kaneko, T.; Li, J.-C.; Lindsy, S.; Moshier, P. M.; Subashi, T. A.; Therrien, M.; Watts, P. C. J. Antibiot. in press.
2. (b) Dabrah, T. T.; Kaneko, T.; Massefski, Jr.; W.; Whipple, E. B. J. Am. Chem. Soc., in press.
3. 2. Roush, W. R. Comprehensive Organic Synthesis; Trost, B. M. Ed.; Pergamon Press: Oxford, 1991, Vol. 5, pp 513-550.
4. 3. Davies, H. M. L. Tetrahedron 1993, 49, 5203.
5. 4. (a) Davies, H. M. L.; McAfee, M. J.; Oldenburg, C. E. M. J. Org. Chem. 1989, 54, 930.
6. (b) Davies, H. M. L.; Doan, B. D. Tetrahedron Lett. 1996, 37, 3967.
7. 5. The synthesis of the vinylcarbenoid precursors was achieved from the corresponding alcohols using the general procedures described in: Davies, H. M. L.; Matasi, J. J.; Ahmed, G. J. Org. Chem. 1996, 61, 2305.
8. 3) δ 10: 0.28 (s, 6 H), 0.91 (s, 9 H), 2.07 (dddd, 1 H, J = 0.9, 1.5, 9.2, 13.1 Hz), 2.19 (dddd, 1 H, J = 3.0, 4.3, 8.2, 13.1 Hz), 2.47 (ddd, 1 H, J = 3.0, 9.2, 18.5 Hz), 2.68 (ddd, 1 H, J = 1.5, 8.2, 18.5 Hz), 2.71 (ddd, 1 H, J = 2.0, 2.0, 16.8 Hz), 3.40 (ddd, 1 H, J = 2.0, 2.0, 16.8 Hz), 3.77 (dddd, 1 H, J = 0.9, 2.0, 2.0, 4.3 Hz), 5.01 (dq, 1 H, J = 2.0, 2.4 Hz), 5.04 (dq, 1 H, J = 2.0, 2.4 Hz); 14a: 0.20 (s, 3 H), 0.23 (s, 3 H), 0.90 (s, 9 H), 1.75 (d, 1 H, J = 17.6 Hz), 2.81 (dd, 1 H, J = 5.4, 17.6 Hz), 4.95 (d, 1 H, J = 12.6 Hz), 4.97 (s, 1 H), 5.04 (d, 1 H, J= 12.6 Hz), 5.28 (d, 1 H, J = 5.4 Hz), 5.36 (s, 1 H); 14b: 0.21 (s, 3 H), 0.24 (s, 3 H), 0.91 (s, 9 H), 1.55 (s, 3 H), 1.76 (d, 1 H, J = 17.4 Hz), 2.81 (dd, 1 H, J = 6.4, 17.4 Hz), 4.95 (s, 2 H), 5.23 (d, 1 H, J = 6.4 Hz), 5.35 (s, 1 H); 14c: 0.20 (s, 3 H), 0.25 (s, 3 H), 0.92 (s, 9 H), 1.97 (d, 1 H, J = 17.6 Hz), 2.76 (dd, 1 H, J = 6.8, 17.6 Hz), 4.08 (d, 1 H, J = 12.7 Hz), 4.13 (d, 1 H, J = 12.7 Hz), 4.44 (d, 1 H, J = 11.7 Hz), 4.50 (d, 1 H, J = 11.7 Hz), 4.89 (s, 1 H), 4.96 (s, 2 H), 5.31 (d, 1 H, J = 6.8 Hz), 7.28-7.38 (m, 5 H); 14d: major isomer 0.21 (s, 3 H), 0.24 (s, 3 H), 0.91 (s, 9 H), 1.00 (t, 3 H, J = 7.5 Hz), 1.73 (d, 1 H, J = 17.7 Hz), 1.78-1.83 (m, 1 H), 1.94-2.01 (m, 1 H), 2.79 (dd, 1 H, J = 4.6, 17.7 Hz), 4.93 (s, 1 H), 4.96 (t, 1 H, J = 6.7 Hz), 5.27 (d, 1 H, J = 4.6 Hz), 5.30 (s, 1 H); minor isomer 0.19 (s, 3 H), 0.23 (s, 3 H), 0.90 (s, 9 H), 0.98 (t, 3 H, J = 7.5 Hz), 1.68 (d, 1 H, J = 17.5 Hz), 1.72-1.81 (m, 1 H), 1.93-2.00 (m, 1 H), 2.79 (dd, 1 H, J = 6.1, 17.5 Hz), 4.91 (s, 1 H), 5.12 (t, 1 H, J = 5.6 Hz), 5.26-5.29 (m, 2H).
9. 7. Davies, H. M. L.; Ahmed, G.; Churchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774.