Synthetic studies on perophoramidine and the communesins: Construction of the vicinal quaternary stereocenters

Journal of Organic Chemistry

Volumn 71, Issue 23, 2006, Pages 8891-8900

  Seo, Jae Hong ^a   Artman III, Gerald D ^a   Weinreb, Steven M ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CARBONYLATION; MOLECULAR DYNAMICS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

CLAISEN REARRANGEMENT; INTRAMOLECULAR HECK CYCLIZATION; SPIROLACTONE SYSTEMS; VICINAL QUATERNARY CARBON;

NITROGEN COMPOUNDS;

COMMUNESIN DERIVATIVE; NATURAL PRODUCT; PEROPHORAMIDINE; SPIRONOLACTONE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CARBONYLATION; CLAISEN REARRANGEMENT; CYCLIZATION; DIASTEREOISOMER; HECK CYCLIZATION; SOLVENT EFFECT; STEREOCHEMISTRY; SYNTHESIS;

HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; HYDROCARBONS, HALOGENATED; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 33750854130     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061660a     Document Type: Article

References (43)

1. Numata, A.; Takahashi, C.; Ito, Y.; Takada, T.; Kawai, K.; Usami, Y.; Matsumura, E.; Imachi, M.; Ito, T.; Hasegawa, T. Tetrahedron Lett. 1993, 34, 2355.
2. (a) Ratnayake, A. S.; Yoshida, W. Y.; Mooberry, S. L.; Hemscheidt, T. K. J. Org. Chem. 2001, 66, 8717.
3. (b) For the retraction of the nomofungin structure, see: Ratnayake, A. S.; Yoshida, W. Y.; Mooberry, S. L.; Hemscheidt, T. K. J. Org. Chem. 2003, 68, 1640.
4. (a) Jadulco, R.; Edrada, R. A.; Ebel, R.; Berg, A.; Schaumann, K.; Wray, V.; Steube, K.; Proksch, P. J. Nat. Prod. 2004, 67, 78.
5. (b) Hayashi, H.; Matsumoto, H.; Akiyama, K. Biosci. Biotechnol. Biochem. 2004, 68, 753.
6. (c) Dalsgaard, P. W.; Blunt, J. W.; Munro, M. H. G.; Frisvad, J. C.; Christophersen, C. J. Nat. Prod. 2005, 68, 258.
7. Some structurally different compounds were initially designated as the same communesins due to simultaneous publication by two groups (see refs 3a and 3b). However, the current communesin nomenclature can be found in ref 3c.
8. (a) Verbitski, S. M.; Mayne, C. L.; Davis, R. A.; Concepcion, G. P.; Ireland, C. M. J. Org. Chem. 2002, 67, 7124.
9. (b) For another related alkaloid see: Verotta, L.; Pilati, T.; Tato, M.; Elisabetsky, E.; Amador, T. A.; Nunes, D. S. J. Nat. Prod. 1998, 61, 392.
10. For recent labeling studies on the biosynthesis of the communesins, see: Wigley, L. J.; Mantle, P. G.; Perry, D. A. Phytochemistry 2006, 67, 561.
11. (a) May, J. A.; Zeidan, R. K.; Stoltz, B. M. Tetrahedron Lett. 2003, 44, 1203.
12. (b) May, J. A.; Stoltz, B. M. Tetrahedron 2006, 62, 5262.
13. Yang, J.; Song, H.; Xiao, X.; Wang, J.; Qin, Y. Org. Lett. 2006, 8, 2187.
14. Crawley, S. L.; Funk, R. L. Org. Lett. 2003, 5, 3169.
15. Fuchs, J. R.; Funk, R. L. J. Am. Chem. Soc. 2004, 126, 5068.
16. Sabahi, A.; Novikov, A.; Rainier, J. D. Angew. Chem., Int. Ed. 2006, 45, 4317.
17. (a) Artman, G. D., III; Weinreb, S. M. Org. Lett. 2003, 5, 1523.
18. (b) Artman, G. D., III. Ph.D. Thesis, The Pennsylvania State University, University Park, PA, 2004.
19. (a) Grigg, R.; Millington, E. L.; Thornton-Pett, M. Tetrahedron Lett. 2002, 43, 2605.
20. (b) Brown, S.; Clarkson, S.; Grigg, R.; Thomas, W. A.; Sridharan, V.; Wilson, D. M. Tetrahedron 2001, 57, 1347.
21. (c) Anwar, U.; Casaschi, A.; Grigg, R.; Sansano, J. M. Tetrahedron 2001, 57, 1361.
22. (d) de Meijere, A.; Bräse, S. J. Organomet. Chem. 1999, 576, 88.
23. (e) Poli, G.; Giambastiani, G.; Heumann, A. Tetrahedron 2000, 56, 5959.
24. (f) Negishi, E.; Ma, S.; Amanfu, J.; Copéret, C.; Miller, J. A.; Tour, J. M. J. Am. Chem. Soc. 1996, 118, 5919.
25. (a) Vetelino, M. G.; Coe, J. W. Tetrahedron Lett. 1994, 35, 219.
26. (b) Coe, J. W.; Vetelino, M. G.; Bradlee, M. J. Tetrahedron Lett. 1996, 37, 6045.
27. Schumacher, R. W.; Davidson, B. S. Tetrahedron 1999, 55, 935.
28. (a) Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1992, 48, 9373.
29. (b) McCort, G.; Hoornaert, C.; Aletru, M.; Denys, C.; Duclos, O.; Cadilhac, C.; Guilpain, E.; Dellac, G.; Janiak, P.; Galzin, A.-M.; Delahaye, M.; Guilbert, F.; O'Connor, S. Bioorg. Med. Chem. 2001, 9, 2129.
30. Lipton, M. F.; Basha, A.; Weinreb, S. M. Org. Synth. 1979, 59, 49.
31. For some examples of reductive Heck reactions, see: (a) Denmark, S. E.; Schnute, M. E. J. Org. Chem. 1995, 60, 1013.
32. (b) Diaz, P.; Gendre, F.; Stella, L.; Charpentier, B. Tetrahedron 1998, 54, 4579.
33. (c) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379 and references cited therein.
34. (d) For a recent example of MeOH acting as a hydride transfer agent, see: Sajiki, H.; Ikawa, T.; Yamada, H.; Tsubouchi, K.; Hirota, K. Tetrahedron Lett. 2003, 44, 171.
35. For preparation of lactones 16 and 31, see Supporting Information in ref 12a.
36. Levin, J. I.; Turos, E.; Weinreb, S. M. Synth. Commun. 1982, 12, 989.
37. (a) Seno, K.; Hagishita, S.; Sato, T.; Kuriyama, K. J. Chem. Soc., Perkin Trans. 1 1984, 2013.
38. (b) Ozlu, Y.; Cladingboel, D. E.; Parsons, P. J. Tetrahedron 1994, 50, 2183.
39. 16 with known lactol i (Mikami, K.; Ohmura, H. Org. Lett. 2002, 4, 3355) to afford benzylidene lactone ii, which was then protected as shown: (Diagram presented).
40. Dai, W.-M.; Lai, K. W. Tetrahedron Lett. 2002, 43, 9377.
41. Similar facial selectivity controlled by the conformation of an α-substituent has been proposed for the alkylation of six-membered lactone enolates: Tomioka, K.; Kawasaki, H.; Yasuda, K.; Koga, K. J. Am. Chem. Soc. 1988, 110, 3597.
42. Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon: New York, 1983; pp 274-284.
43. Imming, P.; Imhof, I.; Zentgraf, M. Synth. Commun. 2001, 31, 3721.