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Volumn 55, Issue 35, 1999, Pages 10673-10684

Construction of 4a,8a-cis-octahydroquinolin-7-one core using an intramolecular aldol type of cyclization: An application to enantioselective total synthesis of lepadin B

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; LEPADIN B; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0033609875     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00603-1     Document Type: Article
Times cited : (47)

References (42)
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    • Cordell, G. A. Ed., Academic Press: New York
    • 1. Daly, J. W.; Garraffo, H. M.; Spande, T. F. In The Alkaloids; Cordell, G.A. Ed., Academic Press: New York, 1993; Vol. 43, pp 185-288; Daly, J. W., In The Alkaloids, Cordell, G. A. Ed., Academic Press: New York, 1998; Vol. 50, pp 141-169.
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    • 5. Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493-6502. This methodology could be applicable to the chiral synthesis of irons-fused decahydroquinoline alkaloid of perhydro-219A; see: McCloskey, P. J.; Schultz, A. G. J. Org. Chem. 1988, 53, 1380-1383.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 6493-6502
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    • 5. Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493-6502. This methodology could be applicable to the chiral synthesis of irons-fused decahydroquinoline alkaloid of perhydro-219A; see: McCloskey, P. J.; Schultz, A. G. J. Org. Chem. 1988, 53, 1380-1383.
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    • 7. Comins, D. L.; Dehghani, A. J. Chem. Soc. Chem. Commun. 1993, 1838-1839. This methodology could be applicable to the chiral synthesis of trans-fused decahydroquinoline alkaloid of (+)-219A; see: Comins, D. L.; Dehghani, A. J. Org. Chem. 1995, 60, 794-795.
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    • 7. Comins, D. L.; Dehghani, A. J. Chem. Soc. Chem. Commun. 1993, 1838-1839. This methodology could be applicable to the chiral synthesis of trans-fused decahydroquinoline alkaloid of (+)-219A; see: Comins, D. L.; Dehghani, A. J. Org. Chem. 1995, 60, 794-795.
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    • note
    • 16. The stereochemistry of the newly formed C-2 and C-3 positions in 8 was anticipated to be 2S, 3R according to our previous investigation on the Michael addition reaction of the similar system; see: refs. 12a and 12f.
  • 32
    • 85030366786 scopus 로고    scopus 로고
    • note
    • 2O in MeOH at 50 °C, no desired cyclization product 12 was isolated.
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    • 21. A 2.5:1 mixture of the diastereomers at the carbinol position was obtained, and the diastereomers were not separated by column chromatography.
  • 37
    • 0000924049 scopus 로고
    • 22. Highly stereoselective 1,4-addition of this type of enone has been reported; see: Polniaszek, R. P.; Dillard, L. W. J. Org. Chem. 1992, 57, 4103-4110; Ibuka, T.; Masaki, N.; Saji, I.; Tanaka, K.; Inubushi, Y. Chem. Pharm. Bull. 1975, 23, 2779-2790.
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    • 22. Highly stereoselective 1,4-addition of this type of enone has been reported; see: Polniaszek, R. P.; Dillard, L. W. J. Org. Chem. 1992, 57, 4103-4110; Ibuka, T.; Masaki, N.; Saji, I.; Tanaka, K.; Inubushi, Y. Chem. Pharm. Bull. 1975, 23, 2779-2790.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.