Total synthesis of (±)-merrilactone A

Angewandte Chemie - International Edition

Volumn 45, Issue 6, 2006, Pages 953-955

  Mehta, Goverdhan ^a   Singh, S Robindro ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

Diastereoselectivity; Natural products; Neurotrophic agents; Terpenoids; Total synthesis

Indexed keywords

DRUG PRODUCTS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

DIASTEREOSELECTIVITY; NATURAL PRODUCTS; NEUROTROPHIC AGENTS; TERPENOIDS; TOTAL SYNTHESIS;

KETONES;

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; LACTONE; MERRILACTONE A; NOOTROPIC AGENT; SESQUITERPENE;

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

ILLICIUM; INDICATORS AND REAGENTS; LACTONES; METHYLATION; NOOTROPIC AGENTS; OXIDATION-REDUCTION; SESQUITERPENES; STEREOISOMERISM;

EID: 32044437636     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200503618     Document Type: Article

References (17)

1. a) For a review on neurotrophic activity, see: F. Hefti, Annu. Rev. Pharmacol. Toxicol. 1997, 37, 239;
2. b) B. Luu, J.-L. G. de Aguilar, C. Girlanda-Junges, Molecules 2000, 5, 1439.
3. a) J.-M. Huang, R. Yokoyama, C.-S. Yang, Y. Fukuyama, Tetrahedron Lett. 2000, 41, 6111;
4. b) J.-M. Huang, R. Yokoyama, C.-S. Yang, Y. Fukuyama, J. Nat. Prod. 2001, 64, 428;
5. c) J.-M. Huang, C.-S. Yang, M. Tanaka, Y. Fukuyama, Tetrahedron 2001, 57, 4691;
6. d) J.-M. Huang, R. Yokoyama, C.-S. Yang, Y. Fukuyama, J. Nat. Prod. 2002, 65, 527.
7. a) V. B. Birman, S. J. Danishefsky, J. Am. Chem. Soc. 2002, 124, 2080;
8. b) M. Inoue, T. Sato, M. Hirama, J. Am. Chem. Soc. 2003, 125, 10772;
9. c) J. Iriondo-Alberdi, J. E. Perea-Buceta, M. F. Greaney, Org. Lett. 2005, 7, 3969;
10. d) K. Harada, H. Kato, Y. Fukuyama, Tetrahedron Lett. 2005, 46, 7407;
11. e) G. Mehta, S. R. Singh, Tetrahedron Lett. 2005, 46, 2079;
12. f) Z. Meng, S. J. Danishefsky, Angew. Chem. 2005, 117, 1535;
13. Angew. Chem. Int. Ed. 2005, 44, 1511.
14. I. Papoutsis, S. Spyroudid, A. Varvoglis, Tetrahedron Lett. 1994, 35, 8449.
15. In a separate effort, we have observed that the cis-1,4-enediol derived from 4 can be enzymatically desymmetrized to provide access to both the enantiomers (unpublished results). Alternatively, enzymatic desymmetrization of 5 or enzymatic resolution of the keto-alcohol 6 can also provide chiral precursors for the asymmetric synthesis of merrilactone A.
16. J. L. Luche, J. Am. Chem. Soc. 1978, 100, 2226.
17. R. H. Grubbs, H. Chang, Tetrahedron 1998, 54, 4413.