Total synthesis and stereochemical revision of (+)-aeruginosin 298-A

Organic Letters

Volumn 2, Issue 26, 2000, Pages 4213-4216

  Wipf, Peter ^a   Methot, Joey Lee ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AERUGINOSIN 298 A; AERUGINOSIN 298-A; ANTITHROMBIN; DRUG DERIVATIVE; LEUCINE;

ARTICLE; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

ANTITHROMBINS; LEUCINE; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 0034727941     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006759x     Document Type: Article

References (36)

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13. Wipf, P.; Kim, Y.; Goldstein, D. M. J. Am. Chem. Soc. 1995, 117, 1106-11112. Goldstein, D. M.; Wipf, P. Tetrahedron Lett. 1996, 37, 739-742 Wipf, P.; Li, W. J. Org. Chem. 1999, 64, 4576-4577. Wipf, P.; Mareska, D. A. Tetrahedron Lett. 2000, 41, 4723-4727.
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17. ad = 11.3 Hz). (aquation presented)
18. Mitsunobu reaction of 9 with BzOH gave the axial benzoate in modest yield (67%) along with elimination product.
19. Use of bulkier bases (e.g., LDA/HMPA) did not provide the epimer but instead a complex mixture, including the Claisen condensation dimer.
20. Heating the unprotected alcohol 4 in basic DMSO led to rapid decomposition.
21. 12 = 8.5 Hz (t).
22. Molander, G. A. Org. React. 1994, 46, 211-367.
23. Griffith, W. P.; Ley, S. V. Aldrichimica Acta 1990, 23, 13-19.
24. D is identical to that prepared by Bonjoch et al. (Bonjoch, J.; Catena, J.; Isabal, E.; Lopez-Canet, M.; Valls, N. Tetrahedron: Asymmetry 1996, 7, 1899-1902).
25. 4 was required to suppress lactam formation.
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28. DEPBT: 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one. Li, H.; Jiang, X.; Ye, Y.; Fan, C.; Romoff, T.; Goodman, M. Org. Lett. 1999, 1, 91.
29. An alternative synthetic strategy whereby the Hpla-Leu side chain was attached first gave identical material.
30. 1H NMR data for 298-A (L-Leu) closely parallel those of 298-B-major, 89-A, 89-B, and desulfated, dimethyl acetal-derivatized 89-A and 89-B (all have D-Leu) but are very different from 298-B-minor (L-Leu); see Supporting Information.
31. Leu-1 confirmed that the leucine residues were indeed in the L-and D-form, respectively (procedure: Adamson, J. G.; Hoang, T.; Crivici, A.; Lajoie, G. A. Anal. Biochem. 1992, 202, 210-214; see Supporting Information).
32. 2O).
33. Based on the well-established binding mode of D-Phe-Pro-Arg chloromethyl ketone (Bode, W.; Turk, D.; Karshikov, A. Protein Sci. 1992, 1, 426-471).
34. The P1-P4 sequences of both 298-A and 98-B occupy the same binding sites: the D-allo-Ile and D-Hpla of 98-B hydrogen bond to Gly216 and Gly219, respectively; the Leu and D-Hpla of 298-A also bind to Gly216 and Gly219, respectively.
35. Sandler, B.; Murakami, M.; Clardy, J. J. Am. Chem. Soc. 1998, 120, 595-596.
36. After submission of this manuscript, another synthesis of aeruginosin 298-A was published that is in agreement with our stereochemical conclusions: Valls, N.; Lopez-Canet, M.; Vallribera, M.; Bonjoch, J. J. Am. Chem. Soc. ASAP, Nov. 1, 2000 Web publication date.