Stereoselective synthesis of musclides A1, A2 and B

Tetrahedron Asymmetry

Volumn 14, Issue 9, 2003, Pages 1127-1131

  Ortiz, Jordi ^a   Ariza, Xavier ^a   Garcia, Jordi ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE; ALKENE; ANTIINFLAMMATORY AGENT; CARDIOTONIC AGENT; METHYLEPHEDRINE; MUSK; SEDATIVE AGENT; ZINC DERIVATIVE;

ARTICLE; COLUMN CHROMATOGRAPHY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REDUCTION; STEREOCHEMISTRY; STEREOISOMERISM; THIN LAYER CHROMATOGRAPHY;

EID: 0037414516     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00120-4     Document Type: Article

References (22)

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16. Reported applications of Carreira's alkynylation to total syntheses are still scarce. See for instance: (a) Bode, J. W.; Carreira, E. M. J. Am. Chem. Soc. 2001, 123, 3611-3612; (b) Bode, J. W.; Carreira, E. M. J. Org. Chem., 2001, 66, 6410-6424; (c) Maezaki, N.; Kojima, N.; Asai, M.; Tominaga, H.; Tanaka, T. Org. Lett. 2002, 4, 2977-2980.
17. Reported applications of Carreira's alkynylation to total syntheses are still scarce. See for instance: (a) Bode, J. W.; Carreira, E. M. J. Am. Chem. Soc. 2001, 123, 3611-3612; (b) Bode, J. W.; Carreira, E. M. J. Org. Chem., 2001, 66, 6410-6424; (c) Maezaki, N.; Kojima, N.; Asai, M.; Tominaga, H.; Tanaka, T. Org. Lett. 2002, 4, 2977-2980.
18. Reported applications of Carreira's alkynylation to total syntheses are still scarce. See for instance: (a) Bode, J. W.; Carreira, E. M. J. Am. Chem. Soc. 2001, 123, 3611-3612; (b) Bode, J. W.; Carreira, E. M. J. Org. Chem., 2001, 66, 6410-6424; (c) Maezaki, N.; Kojima, N.; Asai, M.; Tominaga, H.; Tanaka, T. Org. Lett. 2002, 4, 2977-2980.
19. R/S ratio of 6 was directly determined by HPLC analysis on a chiral column. The absolute configuration of the major enantiomer was assumed to be R on the basis of the work of Carreira et al. (Ref. 6) and confirmed later by chemical correlation with the known monoprotected diol 7.
20. 19F analysis of the corresponding Mosher esters. The configuration of the newly formed stereogenic centers was first determined by the Kakisawa method (Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096) and it always agreed with that expected (Ref. 6). In addition, it should be noted that the absolute configurations were further confirmed by correlation with those of the known, saturated monoprotected diols 7, 10 and 13.
21. 4 reduction of 8 (see Ref. 7).
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