A synthetic pathway to either enantiomer of merrilactone A

Angewandte Chemie - International Edition

Volumn 44, Issue 10, 2005, Pages 1511-1513

  Meng, Zhaoyang ^b   Danishefsky, Samuel J ^a,b  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^b Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

Asymmetric synthesis; Enantioselectivity; Natural products; Regioselectivity; Synthetic methods

Indexed keywords

DEGRADATION; MOLECULAR DYNAMICS; REACTION KINETICS;

ENANTIOCONTROL; ENANTIOMERS; MERRILACTONE A; REGIOCONTROL;

CARBOXYLIC ACIDS;

ACID ANHYDRIDE; GAMMA LACTONE DERIVATIVE; MERRILACTONE A; METHANOL; NATURAL PRODUCT; NEUROTROPHIC FACTOR; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHIRALITY; CLAISEN REARRANGEMENT; DIELS ALDER REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; ESTERIFICATION; HIGH TEMPERATURE; LITHIATION; METHANOLYSIS; METHYLATION; ORGANIC CHEMISTRY; STEREOCHEMISTRY;

LACTONES; SESQUITERPENES; STEREOISOMERISM;

EID: 16244417230     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200462509     Document Type: Article

References (18)

1. V. B. Birman, S. J. Danishefsky, J. Am. Chem. Soc. 2002, 124, 2080; another total synthesis of merrilactone A has since been reported: M. Inoue, T. Sato, M. Hirama, J. Am. Chem. Soc. 2003, 125, 10772.
2. V. B. Birman, S. J. Danishefsky, J. Am. Chem. Soc. 2002, 124, 2080; another total synthesis of merrilactone A has since been reported: M. Inoue, T. Sato, M. Hirama, J. Am. Chem. Soc. 2003, 125, 10772.
3. a) F. Hefti, Annu. Rev. Pharmacol Toxicol. 1997, 37, 239;
4. b) M. R. Bennett, W. G. Gibson, G. Lemon, Auton. Neurosci. 2002, 95, 1;
5. c) P. Lu, A. Blesch, M. H. Tuszynski, J. Comp. Neurol. 2001, 436, 456;
6. d) M. Kaneko, Y. Saito, H. Saito, T. Matsumoto, Y. Matsuda, J. L. Vaught, C. A. Dionne, T. S. Angeles, M. A. Glicksman, N. T. Neff, D. P. Rotella, J. C. Kauer, J. P. Mallamo, R. L. Hudkins, C. Murakata, J. Med. Chem. 1997, 40, 1863;
7. e) C. Backman, G. M. Rose, B. J. Hoffer, M. A. Henry, R. T. Bartus, P. Friden, A. C. Granholm, J. Neurosci. 1996, 16, 5437.
8. a)J.-M. Huang, R. Yokoyama, C-S. Yang, Y. Fukuyama, Tetrahedron Lett. 2000, 41, 6111;
9. b) J.-M. Huang, C.-S. Yang, M. Tanaka, Y. Fukuyama, Tetrahedron 2001, 57, 4691.
10. J. S. Yadav, P. K. Sasmal, Tetrahedron 1999, 55, 5185.
11. S. Ghosh, G. Saha, G. Mostafa, R. Siddhartha, J. Org. Chem. 1992, 57, 7344.
12. Y. V. S. N. Murphy, C. N. Pillai, Synth. Commun. 1996, 26, 2363.
13. a) D. B. Denney, N. Sherman, J. Org. Chem. 1965, 30, 3760;
14. b) S. J. Danishefsky, K. Tsuzuki, J. Am. Chem. Soc. 1980, 102, 6891.
15. P. A. Grieco, S. Gilman, M. Nishizawa, J. Org. Chem. 1976, 41, 1485.
16. M. H. Wu, K. B. Hansen, E. N. Jacobsen, Angew. Chem. 1999, 111, 2167; Angew. Chem. Int. Ed. 1999, 38, 2012.
17. M. H. Wu, K. B. Hansen, E. N. Jacobsen, Angew. Chem. 1999, 111, 2167; Angew. Chem. Int. Ed. 1999, 38, 2012.
18. 3, c = 0.34) for the benzyl ester of ent-16. Although the HPLC data show the enantiospecificity of each reaction that arises from the antipodal catalysts to be identical, the rotations, though opposite, are not equal in magnitude. This suggests the presence of an impurity in one of the specimens. This matter is currently under investigation.