Enantioselective synthesis of a key intermediate aldehyde toward the polyene macrolide filipin III, based on a chiral oxazaborolidinone-promoted asymmetric aldol reaction

Tetrahedron Asymmetry

Volumn 10, Issue 15, 1999, Pages 2871-2879

  Kiyooka, Syun Ichi ^a   Hena, Mostofa A ^a   Goto, Fumitaka ^b  

^a KOCHI UNIVERSITY   (Japan)

^b OTSUKA PHARMACEUTICAL CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXANE DERIVATIVE; ALDEHYDE; FILIPIN;

ARTICLE; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; PARTIAL DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0033618583     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00278-5     Document Type: Article

References (14)

1. Whitfield, G. B.; Brock, T. D.; Ammann, A.; Gottlieb, D.; Carter, H. E. J. Am. Chem. Soc. 1955, 77, 4799-4801.
2. Gale, E. F. Macrolide Antibiotics: Chemistry, Biology, and Practice; Omura, S., Ed.; Academic Press: New York, 1984; p. 425.
3. Richardson, T. I.; Rychnovsky, S. D. J. Org. Chem. 1996, 61, 4219-4231. After our work was finished, we were informed by Prof. S. Rychnovsky that the measured rotation, α, was negative in the original notebook in his laboratory but in the calculation the sign of the rotation was inadvertently dropped.
4. Richardson, T. I.; Rychnovsky, S. D. J. Am. Chem. Soc. 1997, 119, 12360-12361.
5. (a) Kiyooka, S.-i. Rev. Heteroatom Chem. 1997, 17, 245-270.
6. (b) Kiyooka, S.-i.; Hena, M. A. Tetrahedron: Asymmetry 1996, 7, 2181-2184.
7. (c) Kiyooka, S.-i.; Maeda, H. Tetrahedron: Asymmetry 1997, 8, 3371-3374.
8. (d) Kiyooka, S.-i.; Maeda, H.; Hena, M. A.; Uchida, M.; Kim, C.-S.; Horiike, M. Tetrahedron Lett. 1998, 39, 8287-8290.
9. (e) Hena, M. A.; Kim, C.-S.: Horiike, M.; Kiyooka, S.-i. Tetrahedron Lett. 1999, 40, 1161-1164.
10. Boaz, N. W. J. Org. Chem. 1992, 57, 4289-4292.
11. (a) Sullivan, G. R.; Dale, J. A.; Mosher, H. S. J. Org. Chem. 1973, 38, 2143-2147.
12. (b) Yamaguchi, S.; Yasuhara, F.; Kabuto, K. Tetrahedron 1976, 32, 1363-1367.
13. (a) Ha, D.-C; Kil, K.-E.; Choi, K.-S.; Park, H.-S. Tetrahedron Lett. 1996, 37, 5723-5726, and references cited therein.
14. (b) Fráter, G. Tetrahedron Lett. 1981, 22, 425-428.