Stereocontrolled synthesis of the IJK ring segment of yessotoxin

Tetrahedron Letters

Volumn 47, Issue 37, 2006, Pages 6545-6548

  Kadota, Isao ^a   Abe, Takashi ^a   Sato, Yuki ^a   Kabuto, Chizuko ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Cyclization; Polycyclic ethers; Yessotoxin

Indexed keywords

ALCOHOL DERIVATIVE; EPOXIDE; YESSOTOXIN;

ARTICLE; CATALYSIS; CYCLIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 33746819762     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.07.027     Document Type: Article

References (21)

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16. 2 mediated reaction of 11 at 0 °C gave a cyclized product which had no MOMO group on the I ring. Elimination of the MOMO group from the ketyl intermediate would be faster than the cyclization at higher temperature.{A figure is presented}
17. 6) δ 5.05 (dd, J = 10.5, 2.4 Hz, 1H), 4.89 (d, J = 6.6 Hz, 1H), 4.70 (d, J = 6.6;Hz, 1H), 4.57 (m, 1H), 4.14 (d, J = 2.4 Hz, 1H), 3.98-3.90 (m, 3H), 3.76-3.73 (m, 2H), 3.61-3.56 (m, 1H), 3.30-3.25 (m, 4H), 2.55 (dd, J = 15.6, 3.6 Hz, 1H), 2.46 (dd, J = 15.6, 8.0 Hz, 1H), 2.23-2.10 (m, 2H), 1.71 (s, 3H), 1.69-1.48 (m, 2H), 1.16 (s, 3H), 0.98 (s, 9H), 0.93 (t, J = 7.3 Hz, 3H), 0.90 (s, 9H), 0.11 (s, 3H), 0.10 (s, 3H), -0.03 (s, 3H), -0.09 (s, 3H).
18. Schreiber J., Maag H., Hashimoto N., and Eschenmoser A. Angew. Chem., Int. Ed. Engl. 10 (1971) 330-331
19. Takano S., Inomata K., Samizu K., Tomita S., Yanase M., Suzuki M., Iwabuchi Y., Sugihara T., and Ogasawara K. Chem. Lett. (1989) 1283-1284
20. 3) δ 7.60-7.33 (m, 10H), 5.08 (s, 1H), 4.89 (s, 1H), 4.83 (d, J = 6.4 Hz, 1H), 4.69 (d, J = 7.6 Hz, 1H), 4.68 (d, J = 6.4 Hz, 1H), 4.52 (d, J = 12.0 Hz, 1H), 4.46 (d, J = 12.0 Hz, 1H), 4.45 (d, J = 7.6 Hz, 1H), 3.95 (d, J = 2.8 Hz, 1H), 3.91 (s, 1H), 3.83-3.74 (m, 3H), 3.63-3.57 (m, 3H), 3.39-3.32 (m, 3H), 3.35 (s, 3H), 2.53-2.51 (m, 2H), 2.19 (dddd, J = 14.4, 7.6, 7.2, 2.8 Hz, 1H), 2.09-2.02 (m, 2H), 1.70-1.41 (m, 3H), 1.28 (s, 3H), 1.07 (s, 3H).
21. int = 0.059), final R1 = 0.155 and wR (all data) = 0.423. The relatively high R values are due to the fact that four independent molecules are included in the asymmetric unit as well as the crystals being of poor quality. Each four independent molecule adopts a different conformation of the terminal benzyl groups. Complete crystallographic data, as a CIF file, have been deposited with Cambridge Crystallographic Data Centre (CCDC No. 612577). Copies can be obtained free of charge from: The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (e-mail: deposit@ccdc.cam.ac.uk).