Concise synthesis of rodgersinol and determination of the C-10 absolute configuration

Journal of Organic Chemistry

Volumn 72, Issue 2, 2007, Pages 666-668

  Seo, Seung Yong ^a   Jung, Jong Wha ^a   Jung, Jae Kyung ^b   Kim, Nam Jung ^a   Chin, Young Won ^a   Kim, Jinwoong ^a   Suh, Young Ger ^a  

^a Seoul National University   (South Korea)

^b Chungbuk National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC MOIETIES; DIARYL ETHER; ENANTIOSELECTIVE CONSTRUCTION; RODGERSINOL;

AROMATIC COMPOUNDS; COPPER COMPOUNDS; ETHERS; SYNTHESIS (CHEMICAL);

ALCOHOLS;

AROMATIC COMPOUND; CARBON; COPPER; ETHER; ETHYLENE OXIDE DERIVATIVE; METHYL GROUP; PLANT EXTRACT; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; RODGERSIA PODOPHYLLA EXTRACT; RODGERSINOL; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; EPOXIDATION; MEDICINAL PLANT; NONHUMAN; RODGERSIA PODOPHYLLA; STEREOCHEMISTRY;

ALKENES; MOLECULAR STRUCTURE; PHENOLS; SAXIFRAGACEAE; STEREOISOMERISM;

EID: 33846206107     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061980u     Document Type: Article

References (25)

1. Chin, Y.-W.; Park, E. Y.; Seo, S.-Y.; Yoon, K.-D.; Ahn, M.-J.; Suh, Y.-G.; Kim, S. G.; Kim, J. Bioorg. Med. Chem. Lett. 2006, 16, 4600-4602.
2. For a review on the synthesis of 2-arylpropanoic acid, see: Sonawane, H. R.; Bellur, N. S.; Ahuja, J. R.; Kulkarni, D. G. Tetrahedron: Asymmetry 1992, 3, 163-192.
3. For selected reports, see: (a) Hayball, P. J. Drugs 1996, 52, 47-58.
4. (b) Landoni, M. F.; Soraci, A. Curr. Drug. Metab. 2001, 2, 37-51.
5. For reviews on the Suzuki cross-coupling reaction, see: (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
6. (b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147-168.
7. For reviews on asymmetric dihydroxylation, see: (a) Zaitsev, A. B.; Adolfsson, H. Synthesis 2006, 11, 1725-1756.
8. (b) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1996, 94, 2483-2547. In this case, neither the asymmetric epoxidation nor the asymmetric hydroboration was sufficient for application to the stereoselective synthesis of 2-arylpropanol from the diaryl ether 3.
9. For recent reviews on diaryl ether formation, see: (a) Sawyer, J. S. Tetrahedron 2000, 56, 5045-5065.
10. (b) Theil, F. Angew. Chem., Int. Ed. 1999, 38, 2345-2347.
11. (c) Lindley, J. Tetrahedron 1984, 40, 1433.
12. (a) Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937-2940.
13. (b) Chan, D. M. T.; Monaco, K. L.; Wang, R.-P.; Winters, M. P. Tetrahedron Lett. 1998, 39, 2933-2936.
14. The compound 4 was synthesized from the commercially available 4-iodosalicylaldehyde using Wittig olefination.
15. The coupling reaction of an electron-poor phenol with an aldehyde or ketone group instead of an alkyl group, such as 5-bromo-2-hydroxybenzaldehyde or 1-(5-bromo-2-hydroxyphenyl)ethanone, failed to provide the desired product.
16. Crispino, G. A.; Jeong, K.-S.; Kolb, H. C.; Wang, Z.-M.; Xu, D.; Sharpless, K. B. J. Org. Chem. 1993, 58, 3785-3786.
17. The enatiomeric excess (ee) was determined by chiral HPLC. For details, see the Supporting Information.
18. Martinelli, M. J.; Nayyar, N. K.; Moher, E. D.; Dhokte, U. P.; Pawlak, J. M.; Vaidyanathan, R. Org. Lett. 1999, 1, 447-450.
19. (a) Botuha, C. B.; Haddad, M.; Larcheveque, M. Tetrahedron: Asymmetry 1998, 9, 1929-1931.
20. 3-promoted intermolecular backside attack of the methyl nucleophile. Fukumasa, M.; Furuhashi, K.; Umezawa, J.; Takahashi, O.; Hirai, T. Tetrahedron Lett. 1991, 32, 1059-1062.
21. For reports on related conditions, see: (c) Carde, L.; Davies, H.; Geller, T. P.; Roberts, S. M. Tetrahedron Lett. 1999, 40, 5421-5424.
22. (d) Takano, S.; Yanase, M.; Sugihara, T.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1988, 1538-1540 and references therein.
23. For a report on related conditions, see: Miyata, O.; Takeda, N.; Naito, T. Org. Lett. 2004, 6, 1761-1763. and references therein.
24. Yu, J.; Gaunt, M. J.; Spencer, J. B. J. Org. Chem. 2002, 67, 4627-4629.
25. D +12.3 (c 0.05, MeOH).