An enantioselective total synthesis of (+)-cassiol

Tetrahedron Letters

Volumn 37, Issue 51, 1996, Pages 9229-9232

  Irie, Osamu ^a   Fujiwara, Yoko ^a   Nemoto, Hisao ^a   Shishido, Kozo ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CASSIOL;

ARTICLE; ATMOSPHERE; DIASTEREOISOMER; DRUG SYNTHESIS; HYDROLYSIS; METHODOLOGY; STEREOCHEMISTRY;

EID: 0030590987     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02191-0     Document Type: Article

References (17)

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3. 2. Tanaka, S.; Akira, T.; Tabata, M. Yakugaku Zasshi 1984, 104, 601-606; Akira, T.; Tanaka, S.; Tabata, M. Planta medica 1986, 440-443.
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9. 4. For a review, see: Wade, P. A. In Comprehensive Organic Synthesis Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, pp 1124-1133.
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11. 6. MacroModel V4.5: Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-467. The coordinates of the original [3+2] dipolar cycloaddition transition state are strictly constrained during geometrical optimization using MM2″.
12. 7. Evans, E. A. Aldrichimica Acta 1982, 15, 23-32; Gage, J. R.; Evans, D. A. Org. Synth. 1989, 68, 83-91.
13. 7. Evans, E. A. Aldrichimica Acta 1982, 15, 23-32; Gage, J. R.; Evans, D. A. Org. Synth. 1989, 68, 83-91.
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17. 11. The stereochemistry of a newly generated tertiary carbinol center in 16 was established as shown in Scheme 3 by the observation of NOE between one of the methylene protons (δ 3.56, d, J=9.3 Hz) of the hydroxymethyl moiety and an olefinic proton (δ 5.60, dd, J=18.0 and 5.3 Hz).