Heteroatom-directed reverse Wacker oxidations. Synthesis of the reported structure of (-)-herbaric acid

Journal of Organic Chemistry

Volumn 75, Issue 21, 2010, Pages 7388-7392

  Choi, Peter J ^a   Sperry, Jonathan ^a   Brimble, Margaret A ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOMERIC EXCESS; FUNGAL METABOLITES; HETEROATOMS; MICROWAVE-ASSISTED; REGIO-SELECTIVE; STEREOCENTERS; WACKER OXIDATION;

ACIDS; OXIDATION; STEREOCHEMISTRY;

REGIOSELECTIVITY;

ACID; HERBARIC ACID; PHTHALIDE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE; WATER;

ADDITION REACTION; ARTICLE; CHEMICAL STRUCTURE; ENANTIOMER; HYDROBORATION; METABOLITE; MICROWAVE RADIATION; OXIDATION; STEREOCHEMISTRY; SYNTHESIS;

BIOLOGICAL PRODUCTS; FUNGI; HETEROCYCLIC COMPOUNDS, 2-RING; LACTONES; OXIDATION-REDUCTION; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 78049490181     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1016585     Document Type: Article

References (49)

1. Ge, L.; Chan, S-K. S.; Chung, H-S; Li, S.-L. Studies in Natural Products Chemistry; Rahman, A., Ed.; Elsevier: Amsterdam, 2005; Vol. 32, pp 611 - 671.
2. Beck, J. J.; Chou, S.-C. J. Nat. Prod. 2007, 70, 891-900
3. Arnone, A.; Assante, G.; Nasini, G.; De Pava, O. V. Phytochemistry 1990, 29, 613-616
4. Blasko, G.; Gula, D. J.; Shamma, M. J. Nat. Prod. 1982, 45, 105-122
5. Fuska, J.; Uhrin, D.; Proksa, B.; Voticky, Z.; Ruppeldt, J. J. Antibiot. 1986, 39, 1605-1608
6. Palermo, J. A.; Brasco, M. V. R.; Spagnuolo, C.; Seldes, A. M. J. Org. Chem. 2000, 65, 4482-4486
7. Shode, F. O.; Mahomed, A. S.; Rogers, C. B. Phytochemistry 2002, 61, 955-957
8. Barton, D. H. R.; de Vries, J. X. J. Chem. Soc. 1963, 1916-1919
9. Jadulco, R.; Brauers, G.; Edrada, R. A.; Ebel, R.; Wray, V.; Sudarsono; Proksch, P. J. Nat. Prod. 2002, 65, 730-733
10. Kosaka, M.; Sekiguchi, S.; Naito, J.; Uemura, M.; Kuwahara, S.; Watanabe, M.; Harada, N.; Hiroi, K. Chirality 2005, 17, 218-232
11. Pedrosa, R.; Sayalero, S.; Vincente, M. Tetrahedron 2006, 62, 10400-10404
12. Karnik, A. V.; Kamath, S. S. Synthesis 2008, 1832-1834
13. Ramachandran, P. V.; Chen, G.-M.; Brown, H. C. Tetrahedron Lett. 1996, 37, 2205-2208
14. Kitamura, M.; Okhuma, T.; Inoue, S.; Sayo, N.; Kumobayshi, H.; Akutagawa, S.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1998, 110, 629-631
15. Lei, J.-G.; Hong, R.; Yuan, S.-G.; Lin, G.-Q. Synlett 2002, 927-930
16. Witulski, B.; Zimmermann, A. Synlett 2002, 1855-1859
17. Trost, B. M.; Weiss, A. H. Angew. Chem., Int. Ed. 2007, 46, 7664-7666
18. Knepper, K.; Ziegert, R. E.; Brase, S. Tetrahedron 2004, 60, 8591-8603
19. Tanaka, K.; Osaka, T.; Noguchi, K.; Hirano, M. Org. Lett. 2007, 9, 1307-1310
20. Chang, H.-T.; Jeganmohan, M.; Cheng, C.-H. Chem.-Eur. J. 2007, 13, 4356-4363
21. Everaere, K.; Mortreux, A.; Carpentier, J.-F. Adv. Synth. Catal. 2003, 345, 67-77
22. Zhang, H.; Zhang, S.; Liu, L.; Luo, G.; Duan, W.; Wang, W. J. Org. Chem. 2010, 75, 368-374
23. Phan, D. H. T.; Kim, B.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 15608-15609
24. Willis, M. C. Angew. Chem., Int. Ed. 2010, 49, 6026-6027
25. Muzart, J. Tetrahedron 2007, 63, 7505-7521
26. Brown, H. C.; Zweifel, G. J. Am. Chem. Soc. 1959, 81, 247
27. Bachu, P.; Gibson, J. S. S.; Sperry, J.; Brimble, M. A. Tetrahedron: Asymmetry 2007, 18, 1618-1624
28. Lock, G.; Nottes, G. Monatsch. Chem. 1936, 68, 51-57
29. Merlic, C. A.; Aldrich, C. C.; Albaneze-Walker, J.; Saghatelian, A.; Mammen, J. J. Org. Chem. 2001, 66, 1297-1309
30. Kazlauskas, R. J.; Weissfloch, A. N. E.; Rappaport, A. T.; Cuccia, L. A. J. Org. Chem. 1991, 56, 2656-2665
31. Robinson, J. E.; Brimble, M. A. Chem. Commun. 2005, 1560-1562
32. Robinson, J. E.; Brimble, M. A. Org. Biomol. Chem. 2007, 5, 2572-2582
33. Brimble, M. A.; Bryant, C. J. Chem. Commun. 2006, 4506-4508
34. Brimble, M. A.; Bryant, C. J. Org. Biomol. Chem. 2007, 5, 2858-2866
35. Keaton, K. A.; Phillips, A. J. Org. Lett. 2007, 14, 2717-2719
36. Tsuji, J. Synthesis 1984, 369-384
37. Bose, A. K.; Krishnan, L.; Wagle, D. R.; Manhas, M. S. Tetrahedron Lett. 1986, 27, 5955-5958
38. Lai, J.-Y.; Shi, X.-X.; Dai, L.-X. J. Org. Chem. 1992, 57, 3485-3487
39. Pellissier, H.; Michellys, P.-Y.; Santelli, M. Tetrahedron Lett. 1994, 35, 6481-6484
40. Pellissier, H.; Michellys, P.-Y.; Santelli, M. Tetrahedron 1997, 53, 7577-7586
41. Pellissier, H.; Michellys, P.-Y.; Santelli, M. Tetrahedron 1997, 53, 10733-10742
42. Kang, S.-Y.; Jung, K.-Y.; Chung, J.-U.; Namkoong, E.-Y.; Kim, T.-H. J. Org. Chem. 1995, 60, 4678-4679
43. Weiner, B.; Baeza, A.; Jerphagnon, T.; Feringa, B. L. J. Am. Chem. Soc. 2009, 131, 9473-9474
44. Ho, T. L.; Chang, M. H.; Chen, C. Tetrahedron Lett. 2003, 44, 6955-6957
45. Keinan, E.; Seth, K. K.; Lamed, R. J. Am. Chem. Soc. 1986, 108, 3474-3480
46. Gaunt, M. J.; Yu, J.; Spencer, J. B. Chem. Commun. 2001, 1844-1845
47. Wright, J. A.; Gaunt, M. J.; Spencer, J. B. Chem.-Eur. J. 2006, 12, 949-955
48. Hosokawa, T.; Ohta, T.; Kanayama, S.; Murahashi, S.-I. J. Org. Chem. 1987, 52, 1758-1764
49. Kang, S.-K.; Jung, K.-Y.; Chung, J. U.; Namkoong, E. Y.; Kim, T.-H. J. Org. Chem. 1995, 60, 4678-4679