Synthesis of ent-thallusin

Organic Letters

Volumn 8, Issue 10, 2006, Pages 2123-2126

  Gao, Xiaolei ^a   Matsuo, Yoshihide ^b   Snider, Barry B ^a  

^a BRANDEIS UNIVERSITY   (United States)

^b MARINE BIOTECHNOLOGY INSTITUTE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENE; PALLADIUM; PYRIDINE DERIVATIVE; SCLAREOL; THALLUSIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; GREEN ALGA; STEREOISOMERISM; SYNTHESIS;

ALGAE, GREEN; CHLOROPHYTA; DITERPENES; MOLECULAR STRUCTURE; PALLADIUM; PYRIDINES; STEREOISOMERISM;

EID: 33744720396     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0605777     Document Type: Article

References (21)

1. Matsuo, Y.; Imagawa, H.; Nishizawa, M.; Shizuri, Y. Science 2005, 307, 1598.
2. Zimmermann, N.; Meggers, E.; Schultz, P. G. Bioorq. Chem. 2004, 32, 13-25.
3. Leite, M. A. F.; Sarragiotto, M. H.; Imamura, P. M.; Marsaioli, A. J. J. Org. Chem. 1986, 51, 5409-5410.
4. Barrero, A. F.; Alvarez-Manzaneda, E. J.; Altarejos, J.; Salido, S.; Ramos, J. M. Tetrahedron 1993, 49, 10405-10412.
5. Aricu, A. N.; Andreeva, I. Yu.; Vlad, P. F. Russ. Chem. Bull. 1996, 45, 2645-2648;
6. Izv. Akad. Nauk, Ser. Khim. 1996, 2785-2789;
7. Chem. Abstr. 1997, 126, 157649m.
8. The spectral data are analogous to those of related compounds: Faivre, V.; Lila, C.; Saroli, A.; Doutheau, A. Tetrahedron 1989, 45, 7765-7782.
9. Zhang, F. J.; Li, Y. L. Synthesis 1993, 565-567.
10. Ganem, B.; Boeckman, R. K., Jr. Tetrahedron Lett. 1974, 917-920.
11. Homsi, F.; Robin, S.; Rousseau, G. Org. Synth. 1999, 77, 206-211.
12. Corey, E. J.; Gilman, N. W.; Ganem, B. E. J. Am. Chem. Soc. 1968, 90, 5616-5617.
13. Benaglia, M.; Toyota, S.; Woods, C. R.; Siegel, J. S. Tetrahedron Lett. 1997, 38, 4737-4740.
14. Parrish, J. P.; Flanders, V. L.; Floyd, R. J.; Jung, K. W. Tetrahedron Lett. 2001, 42, 7729-7731.
15. Farina, V.; Kapadia, S.; Krishnan, B.; Wang, C.; Liebeskind, L. S. J. Org. Chem. 1994, 59, 5905-5911.
16. Thermal Stille coupling of 4 and 5 at 90 °C gave 14 in about 30% yield at short reaction times (20, 30 min) and 50-60% yield with longer reaction times (2, 2.5 h).
17. Klyne, W.; Buckingham, J. Atlas of Stereochemistry-Absolute Configurations of Organic Molecules; Oxford University Press: New York, 1978; pp 108-111.
18. Torrenegra, R.; Robles, J.; Waibel, R.; Löwel, M.; Achenbach, H. Phytochemistry 1994, 35, 195-199.
19. Nakano, T.; Djerassi, C. J. Org. Chem. 1961, 26, 167-173.
20. Nunes, F. M. N.; Imamura, P. M. J. Braz. Chem. Soc. 1996, 7, 181-186.
21. Geuns, J. M. C. Phytochemistry 2003, 64, 913-921.