Synthetic studies towards pateamine, a novel thiazole-based 19-membered bis-lactone from Mycale sp

Tetrahedron Letters

Volumn 37, Issue 50, 1996, Pages 9107-9110

  Critcher, Douglas J ^a   Pattenden, Gerald ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFUNGAL AGENT; PATEAMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

MYCALE; STURNUS VULGARIS;

EID: 0030577502     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02098-9     Document Type: Article

References (20)

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2. 2. Rzasa, R. M.; Romo, D.; Stirling, D. J.; Blunt, J. W.; Munroe, M. H. G. Tetrahedron Lett. 1995, 36, 5307.
3. 3. Blincoe, S. N., MSc Thesis, University of Canterbury, New Zealand, 1994 (quoted in ref. 2). For complementary studies see: Maddock, J., PhD Thesis, University of Nottingham, England, 1993.
4. 4. Saito, S.; Hasegawa, T.; Inaba, M.; Nishida, R.; Fujii, T.; Normizu, S.; Morimake, T. Chem. Lett. 1984, 1389.
5. 5. For the Holzapfel modification of the Hantzsch thiazole synthesis see: (a) Bredenkamp, M. W.; Holzapfel, C. W.; van Zyl, W. J. Syn. Commun. 1990, 20, 2235;
6. (b) Bredenkamp, M. W.; Holzapfel, C. W.; Synman, R. M; van Zyl, W. J. Synth. Commun. 1992, 22, 3029.
7. This procedure has previously been used in our laboratories, see: (c) Pattenden, G.; Thom, S. M. Synlett, 1993, 215;
8. (d) Boden, C. D. J.; Pattenden, G.; Ye, T. Synlett, 1995, 417.
9. 3, 400MHz) 7.21 (1H, d, J=12.8 Hz), 6.86 (1H, m), 6.76 (1H, s), 6.74 (1H, d, J=12.8 Hz), 5.96 (1H, s), 5.76 (1H, d, J=15.6 Hz), 5.28 (1H, m), 5.08 (1H, m), 3.78 (2H, m), 3.41 (1H, dd, J=14.9, 5.3 Hz), 3.32 (1H, dd, J=14.9, 7.0 Hz), 3.10 (1H, m), 2.70 (1H, m), 2.53 (1H, dd, J=13.9, 7.9 Hz), 2.40 (1H, m), 2.37 (1H, dd, J=13.9, 5.6 Hz), 1.86 (3H, s), 1.50 (6H, m), 1.30 (6H, m), 1.28 (3H, d, J=6.7 Hz), 1.22 (3H, d, J=6.5 Hz), 1.05-0.85 (15H, m), 0.90 (9H, s), 0.05 (3H, s), 0.04 (3H, s).
10. 7. Rand, C. L.; Van Horn, D. E.; Moore, M. W.; Negishi, E. J. Org. Chem. 1981, 46, 4093.
11. 8. The enantiomerically pure alkyne 11 was prepared from the addition of the ethylenediamine complex of lithium acetylide to S-propylene oxide in dimethylsulfoxide, see: Adams, M. A.; Duggan, A. J.; Smolanoff, J.; Meinwald, J. J. Am. Chem. Soc. 1979, 101, 5364. Also see ref. 2 above.
12. 9. Neises, B.; Steglich, W. Angew. Chem Int. Ed. Engl. 1978, 17, 522.
13. 10. Ethyl Z-3-(tributylstannyl)propenoate was prepared from ethyl propiolate, see: Gomez, A. M.; Lopez, J. C.; Fraser-Reid, B.; J. Chem. Soc. Perkin Trans. 1, 1994, 1689. Saponification of the ethyl ester with lithium hydroxide then gave Z-3-tributylstannylpropenoic acid.
14. 11. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989.
15. 12. (a) Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585;
16. (b) Farina, V. Pure & Appl. Chem. 1996, 68, 73.
17. +): 520.2553, found m/z 520.2583.
18. 14. For intramolecular Stille reactions applied to natural product synthesis from our laboratories, see for example: (a) ref. 5(c) above;
19. (b) Boyce, R. J.; Pattenden, G. Tetrahedron Lett., 1996, 37, 3501;
20. (c) Entwistle, D. A.; Jordon, S. I.; Montgomery, J.; Pattenden, G. J. Chem. Soc. Perkin Trans. 1, 1996, 1315. Reference 14(c) also provides a bibliography of other examples of the use of the intramolecular Stille reaction in synthesis.