Mycothiazole: Synthesis of the C8-C18 subunit and further evidence of the (Z)-Δ14 double bond configuration

European Journal of Organic Chemistry

Volumn , Issue 6, 2007, Pages 934-942

  Rega, Miriam ^a   Candal, Paloma ^a   Jiménez, Carlos ^a   Rodríguez, Jaime ^a  

^a UNIVERSITY OF A CORUÑA   (Spain)

Author keywords

Configuration determination; Cross metathesis; Sulfur heterocycles

Indexed keywords

EID: 34250669678     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600671     Document Type: Article

References (19)

1. P. Crews, Y. Kakou, E. Quiñoá, J. Am. Chem. Soc. 1988, 110, 4365-1368.
2. A. Cutignano, I. Bruno, G. Bifulco, A. Casapullo, C. Debitus, L. Gomez-Paloma, R. Riccio, Eur. J. Org. Chem. 2001, 775-778.
3. [17]
4. a) H. Sugiyama, F. Yokokawa, T. Shioiri, Org. Lett. 2000, 2, 2149-2152;
5. b) H. Sugiyama, F. Yokokawa, T. Shioiri, Tetrahedron 2003, 59, 6579-6593.
6. a) A. Le Flohic, C. Meyer, J. Cossy, Org. Lett. 2005, 7, 339-342;
7. b) A. Le Flohic, C. Meyer, J. Cossy, Tetrahedron 2006, 62, 9017-9037.
8. G. Mahler, G. Sierra, S. Dematteis, J. Saldaña, L. Domínguez, E. Manta, Bioorg. Med. Chem. Lett. 2006, 16, 1309-1311.
9. R. N. Sonnenschein, T. A. Johnson, K. Tenney, F. A. Valeriote, P. Crews, J. Nat. Prod. 2006, 69, 145-147.
10. S. Rodríguez-Conesa. P. Candal, C. Jiménez, J. Rodríguez, Tetrahedron Lett. 2001, 42, 6699-6702.
11. B. S. Pedersen, S. O. Lawesson, Tetrahedron 1979, 35, 2433-2437.
12. A. Dondoni, P. Merino, Comprehensive Heterocyclic Chemistry II (Eds.: A. R. Katritzky, W. Rees, E. F. V. Scriven), Pergamon, 1996, vol. 3, pp. 432-434.
13. a) I. Pérez, J. Pérez Sestelo, L. Sarandeses, J. Am. Chem. Soc. 2001, 123, 4155-4160;
14. b) D. Rodríguez, J. Pérez Sestelo, L. A. Sarandeses, J. Org. Chem. 2004, 69, 8136-8139.
15. [13]) we did not observe homodimerization of 12a, which is a good candidate for selective cross metathesis with type II partners.
16. A. K. Chatterjee, T. L. Choi, P. Daniel, R. H. Grubbs, J. Am. Chem. Soc. 2003, 125, 11360-11370.
17. A. J. Vernall, A. D. Abell, Aldrichimica Acta 2003, 36, 93-105.
18. An E/Z ratio of 7:1 was deduced by 2D integration of the edited gHSQC experiment from the crude metathesis reaction product.
19. P. Crews, J. Rodriguez, M. Jaspars, Organic Structural Analysis, Oxford University Press, 1988, pp. 78-79.