Enantioselective allyltitanations: Synthesis of the proposed structures for passifloricin A

Tetrahedron Letters

Volumn 44, Issue 24, 2003, Pages 4471-4473

  BouzBouz, Samir ^a   Cossy, Janine ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFUNGAL AGENT; PASSIFLORICIN A; PLANT EXTRACT; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; NONHUMAN; PASSION FRUIT; PLANT; RING CLOSING METATHESIS; STEREOCHEMISTRY;

EID: 0038065656     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01024-4     Document Type: Article

References (14)

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5. The enantiomeric excess of homoallylic alcohol 2 was determined by HPLC analysis ( Waters 590 chromatograph coupled with a Varian UV detector, λ=220 nm), Chiralpak-OD-H column (hexane/isopropanol: 98/2).
6. Trost B.M., Belletire J.L., Godleski S., McDougal P.G., Balkovec J.M., Baldwin J.J., Christy M.E., Ponticello G.S., Varga S.L., Springer J.P. J. Org. Chem. 51:1986;2370.
7. 13C NMR δ: 134.2 (d), 117.9 (t), 72.7 (d), 71.8 (d), 42.4 (t), 42.2 (t), 38.0 (t), 31.8 (t), 29.5 (9t), 29.2 (t), 25.2 (t), 22.5 (t), 13.9 (q).
8. 13C NMR δ: 134.2 (d), 116.8 (t), 98.2 (s), 68.8 (d), 68.6 (d), 40.7(t), 36.3-31.8-29.6-29.5-29.4-29.2-24.8-22.5 (15t), 30.1 (q), 19.6 (q), 13.9 (q).
9. Rychnovsky S.D., Rogers B.N., Richardson T.I. Acc. Chem. Res. 31:1998;9.
10. 13C NMR δ: 134.9 (d), 116.7 (t), 69.4 (2d), 67.4 (d), 45.9 (t), 45.7 (t), 42.0 (t), 36.4 (t), 31.8 (t), 29.7-29.6-29.5-29.4-29.2 (10t), 25.8 (6q), 25.6 (3q), 25.0 (t) 22.5 (t), 17.9 (3s), 13.9 (q), -3.1 (q), -3.9 (q), -4.2 (q), -4.3 (q), -4.4 (q), -4.6 (q).
11. Fürstner A. Angew. Chem., Int. Ed. 39:2000;3012.
12. Trnka T., Grubbs R.H. Acc. Chem. Res. 34:2001;18.
13. 13C NMR (400 MHz) δ: 164.2 (s), 145.4 (d), 121.2 (d), 76.7 (d), 73.4 (d), 70.5 (d), 66.0 (d), 43.0 (t), 42.5 (t), 41.9 (t), 38.4 (t), 31.9-29.7-29.6-29.4-25.3-22.7 (14t), 14.1 (q).
14. 13C NMR (400 MHz) δ: 165.2 (s), 146.0 (d), 121.6 (d), 75.5 (d), 73.6 (d), 70.9 (d), 64.6 (d), 43.8 (t), 43.0 (t), 42.9 (t), 38.7 (t), 32.3-30.3-30.1-30.0-29.7-25.7-23.0 (14t), 14.5 (q).