Synthesis of (+)- And (-)-monanchorin

Organic Letters

Volumn 11, Issue 4, 2009, Pages 1031-1032

  Yu, Min ^a   Snider, Barry B ^a  

^a BRANDEIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; FUSED HETEROCYCLIC RINGS; GUANIDINE DERIVATIVE; MONANCHORIN;

ANIMAL; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE; SPONGE (PORIFERA); STEREOISOMERISM; SYNTHESIS;

ANIMALS; ANTINEOPLASTIC AGENTS; BICYCLO COMPOUNDS, HETEROCYCLIC; CATALYSIS; GUANIDINES; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PORIFERA; STEREOISOMERISM;

EID: 62749098709     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802981h     Document Type: Article

References (17)

1. (1) Meragelman, K. M.; McKee, T. C.; McMahon, J. B. J. Nat. Prod. 2004, 67, 1165-1167.
2. (2) (a) Takagi, Y.; Kawashima, O.; Tsuchiya, T.; Sano, H.; Umezawa, S. Bull. Chem. Soc. Jpn. 1976, 49, 3108-3112.
3. (b) Nakamura, H.; Iitaka, Y. Actca. Crystallogr. 1978, B34, 3384-3387.
4. (3) (a) Snider, B. B.; Faith, W. C. J. Am. Chem. Soc. 1984, 106, 1443-1445.
5. (b) Snider, B. B.; Shi, Z. J. Am. Chem. Soc. 1994, 116, 549-557.
6. (c) Snider, B. B.; Chen, J. Tetrahedron Lett. 1998, 39, 5697-5700.
7. (d) Yu, M.; Pochapsky, S. S.; Snider, B. B. J. Org. Chem. 2008, 72, 9065-9074.
8. (4) For a similar reaction with methoxide, see the conversion of 11 via an epoxy aldehyde to 12 in: Hori, K.; Hikage, N.; Inagaki, A.; Mori, S.; Nomura, K.; Yoshii, E. J. Org. Chem. 1992, 57, 2888-2902.
9. 4, epoxidation with mCPBA, and oxidation of the alcohol with Dess-Martin periodinane.
10. (6) Wang, Z.-X.; Tu, Y.; Frohn, M.; Zhang, J.-R.; Shi, Y. J. Am. Chem. Soc. 1997, 119, 11224-11235.
11. 13C NMR spectrum in the presence of europium tris[3- (trifluoromethylhydroxymethylene) - (+) - camphorate].
12. (8) (a) Le Merrer, Y.; Gauzy, L.; Gravier-Pelletier, C.; Depezay, J.-C. Bioorg. Med. Chem. 2000, 8, 307-320.
13. (b) Dennis, M.; Hall, L. M.; Murphy, P. J.; Thornhill, A. J.; Nash, R.; Winters, A. L.; Hursthouse, M. B.; Light, M. E.; Horton, P. Tetrahedron. Lett. 2003, 44, 3075-3080.
14. (9) Fritsche-Lang, W.; Wilharm, P.; Hadicke, E.; Fritz, H.; Prinzbach, H. Chem. Ber. 1985, 118, 2044-2078.
15. (10) Ma, D.; Xia, C.; Jiang, J.; Zhang, J. Org. Lett. 2001, 3, 2189-2191.
16. (11) The regiochemistry of 14 and 15 was established by COSY correlations from H-1 through H-4.
17. (12) Zhao, M.-X.; Shi, Y. J. Org. Chem. 2006, 71, 5377-5379.