Synthesis of the AB ring system of gambierol

Tetrahedron Letters

Volumn 39, Issue 35, 1998, Pages 6365-6368

  Kadota, Isao ^a   Park, Choul Hong ^a   Ohtaka, Manabu ^a   Oguro, Nao ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 DEOXYRIBOSE; CIGUATOXIN; GAMBIEROL; POLYCYCLIC HYDROCARBON; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; NUCLEAR OVERHAUSER EFFECT; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032572856     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01310-0     Document Type: Article

References (10)

1. (1) For a recent review, see: Yasumoto, T.; Murata, M. Chem. Rev. 1993, 93, 1897-1909.
2. (2) For recent reviews, see: (a) Alvarez, E.; Candenas, M.-L.; Pérez, R.; Ravelo, J. L.; Martín, J. D. Chem. Rev. 1995, 95, 1953-1980.
3. (b) Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 589-607.
4. (3) Satake, M.; Murata, M.; Yasumoto, T. J. Am. Chem. Soc. 1993, 115, 361-362.
5. (4) For a recent review on the stereoselective allylation of aldehydes, see: Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207-2293.
6. (5) (a) Nicolaou, K. C.; Nugiel, D. A.; Couladouros, E.; Hwang, C.-K. Tetrahedron 1990, 46, 4517-4552.
7. (b) Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E.; Nugiel, D. A.; Abe, Y.; Reddy, K. B.; Defrees, S. A.; Reddy, D. R.; Awartani, R. A.; Conley, S. R.; Rutjes, F. P. J. T.; Theodorakis, E. A. J. Am. Chem. Soc. 1995, 117, 10227-10238.
8. (6) For a recent example of the synthesis of cyclic ethers via the intramolecular hetero-Michael reaction, see: Betancort, J. M.; Martín, V. S.; Padrón, J. M.; Palazón, J. M.; Ramírez, M. A.; Soler, M. A. J. Org. Chem. 1997, 62, 4570-4583 and references cited therein.
9. (7) Tanaka, S.; Oguri, H.; Hishiyama, S.; Oishi, T.; Hirama, M. The 70th Annual Meeting of the Chemical Society of Japan 1996. The conditions employed gave a better result than the usual conditions (NaH in THF) for this type of transformations.
10. 3) δ 7.34-7.24 (m, 10H), 5.00 (t, J = 2.9 Hz, 1H), 4.63 (d, J = 11.5 Hz, 1H), 4.45 (s, 2H), 4.44 (d, J = 11.5Hz, 1H), 4.20-4.24 (m, 1H), 3.70 (s, 3H), 3.62 (dd, J = 12.7, 3.5 Hz, 1H), 3.59-3.52 (m, 1H), 3.51 (dd. J = 11.3, 4.6Hz, 1H), 2.54 (dd, J = 15.4, 7.9 Hz, 1H), 2.39 (dd, J = 15.4, 4.9Hz, 1H), 2.16 (ddd, J = 11.8, 4.0, 4.0 Hz, 1H), 2.01 (s, 3H), 2.00-1.71 (m, 6H), 1.31 (s, 3H), 1.28 (s, 3H).