Use of ketene dithioacetal as a latent carboxylic acid in the macrolactonization applicable to the synthesis of dilactonic pyrrolizidine alkaloids

Journal of Organic Chemistry

Volumn 61, Issue 4, 1996, Pages 1473-1474

  Chou, Wen Chih ^a   Fang, Jim Min ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLIZIDINE ALKALOID;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; TECHNIQUE;

EID: 0029971742     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951363y     Document Type: Article

References (27)

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13. For reviews of macrolide syntheses, see; (a) Masamune, S.; Bates, G. S.; Corcoran, J. W. Angew. Chem., Int. Ed. Engl. 1977, 16, 585. (b) Nicolaou, K. C. Tetrahedron 1977, 33, 683. (c) Back, T. G. Terahedron 1977, 33, 3041.
14. For reviews of macrolide syntheses, see; (a) Masamune, S.; Bates, G. S.; Corcoran, J. W. Angew. Chem., Int. Ed. Engl. 1977, 16, 585. (b) Nicolaou, K. C. Tetrahedron 1977, 33, 683. (c) Back, T. G. Terahedron 1977, 33, 3041.
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18. Use of 4-DMAP to facilitate macrolaetonization: (a) Niwa, H.; Okamoto, O.; Yamada, K. Tetrahedron Lett. 1988, 29, 5139. The use of Ag(I) is superior to other metal ions in the transformation of thioesters to esters; see (b) Gerlach, H.; Thalmann, A. Helv. Chim. Acta 1974, 57, 293.
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21. 3) δ 15.31 (q), 20.65 (q), 33.68 (t), 37.55 (t), 38.25 (d), 54.35 (t), 56.10 (t), 59.99 (t), 66.45 (t), 72.00 (d), 78.20 (d), 79.44 (s), 127.37 (d, 3 C), 128.25 (d, 2 C), 129.70 (d), 131.77 (s), 138.64 (s), 169.64 (s), 173.58 (s).
22. Philips, K. D.; Zemlicka, J.; Horowitz, J. P. Carbohydr. Res. 1973, 30, 281.
23. Trost, B. M.; Chung, J. Y. L. J. Am. Chem. Soc. 1985, 107, 4586.
24. Johansson, R. ; Samuelsson, B. J. Chem. Soc., Perkin Trans. 1 1984, 2371.
25. Pandey, G.; Krishna, A. Synth. Commun. 1988, 18, 2309.
26. 3) δ 0.99 (d, J = 6.9 Hz, 3 H), 1.27 (t, J = 7.2 Hz, 3 H), 1 41 (s, 3 H), 2.08-2.15 (m, 2 H), 2.20 (s, 3 H), 2.78-2.87 (m, 4 H), 3.11-3.20 (m, 1 H), 4.13 (q, J = 7.2 Hz, 2 H), 4.48, 4.62 (AB quartet, J = 10.4 Hz, 2 H), 5.94 (d, J = 10.0 Hz, 1 H).
27. Pojer, P. M.; Angyal, S. J. Aust. J. Chem. 1978, 31, 1031.