Synthesis of cordiaquinones B, C, J, and K on the basis of a bioinspired approach and the revision of the relative stereochemistry of cordiaquinone C

Journal of Organic Chemistry

Volumn 73, Issue 12, 2008, Pages 4484-4490

  Arkoudis, Elias ^a   Stratakis, Manolis ^a  

^a UNIVERSITY OF CRETE   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; BIOCHEMICAL ENGINEERING; BIOCHEMISTRY; CHEMICAL REACTIONS; CHEMICALS; CHEMISTRY; KETONES; PAINTING; STEREOCHEMISTRY;

AMERICAN CHEMICAL SOCIETY (ACS); BENZOQUINONE (BQ); BIO INSPIRED APPROACH; BIO-INSPIRED; CHEMICAL EQUATIONS; DIELS-ALDER (DA) REACTION; FARNESENE; KEY REACTIONS; NAPHTHOQUINONE; SYNTHESIS (OF CHIRAL IONIC LIQUIDS); TERPENOID; TRANS FARNESOL;

SYNTHESIS (CHEMICAL);

ALKADIENE; BENZOQUINONE; CORDIAQUINONE B; CORDIAQUINONE C; CORDIAQUINONE J; CORDIAQUINONE K; EPOXIDE; FARNESENE; FARNESOL; NAPHTHOQUINONE; NEROLIDOL; QUINONE DERIVATIVE; TERPENOID;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; DIELS ALDER REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

CATALYSIS; CYCLIZATION; MAGNETIC RESONANCE SPECTROSCOPY; QUINONES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STEREOISOMERISM;

EID: 45249107493     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800355y     Document Type: Article

References (23)

1. Bieber, L. W.; Messana, I.; Lins, S. C. N.; da Silva Filho, A. A.; Chiappeta, A. A.; De Mello, J. F. Phytochemistry 1990, 29, 1955-1959.
2. Bieber, L. W.; Krebs, H. C.; Schafer, W. Phytochemistry 1994, 35, 1027-1028.
3. Ioset, J.-R.; Marston, A.; Gupta, M. P.; Hostettmann, K. Phytochemistry 1998, 47, 729-734.
4. Ioset, J.-R.; Marston, A.; Gupta, M. P.; Hostettmann, K. Phytochemistry 2000, 53, 613-617.
5. The possibility that the naphthoquinone moiety of cordiaquinones arises from a polyketide pathway can not be excluded. For the biogenesis of quinones through polyketides, see: Bringmann, G.; Noll, T. F.; Guider, T. A. M.; Grune, M.; Dreyer, M.; Wilde, C.; Pankewitz, F.; Hilker, M.; Payne, G. D.; Jones, A. L.; Goodfellow, M.; Fiedler, H.-P. Nat. Chem. Biol. 2006, 2, 429-433.
6. For the role of Diels-Alder reaction in biogenetic pathways, see: Stocking, E. M.; Williams, R. M. Angew. Chem., Int. Ed. 2003, 42, 3078-3115.
7. Bocchi, M.; Garlaschelli, L.; Vidari, G.; Mellerio, G. J. Nat. Prod 1992, 55, 428-431.
8. Tsangarakis, C.; Arkoudis, E.; Raptis, C.; Stratakis, M. Org. Lett. 2007, 9, 583-586.
9. Yajima, A.; Saitou, F.; Sekimoto, M.; Maetoko, S.; Nukada, T.; Yabuta, G. Tetrahedron 2005, 61, 9164-9172.
10. Otera, J.; Niibo, Y.; Okuda, K. Chem. Lett. 1986, 11, 1829-1832.
11. Castro, M. A.; del Corral, J. M. M.; Gordaliza, M.; Garcia, P. A.; Gamito, A. M.; Gualberto, S. A.; Batista, R.; San Feliciano, A. Synthesis 2005, 3202-3208.
12. Vougioukalakis, G. C.; Orfanopoulos, M. Synlett 2005, 713-731.
13. For the reaction of α-cyclogeranyl derivatives, such as 10, with PTAD, see: Tsangarakis, C.; Zaravinos, I.-P.; Stratakis, M. Synlett 2005, 1857-1860.
14. For a similar isolation of one among other regioisomeric alkenes using their reaction with m-CPBA, see: Basabe, P.; Bodero, O.; Marcos, I. S.; Diez, D.; de Roman, M.; Blanco, A.; Urones, J. G. Tetrahedron 2007, 63, 11838-11843.
15. Nemoto, T.; Ohshima, T.; Shibasaki, M. Tetrahedron 2003, 59, 6889-6897.
16. van Tamelen, E. E. Acc. Chem. Res. 1975, 8, 152-158.
17. Filho; A, A.; Lima, R. M. O. C.; Nascimento, S. C.; Silva, E. C.; Andrade, M. S. A. S.; Lins, S. C. N.; Bieber, L. W. Fitoterapia 1993, 64, 78-80.
18. (a) van Tamelen, E. E.; Coates, R. M. Bioorg. Chem. 1982, 11, 171-196.
19. (b) Hoshino, T.; Sakai, Y. Tetrahedron Lett. 2001, 42, 7319-7323.
20. Kuramochi, T.; Asaoka, M.; Ohkubo, T.; Tahei, H. Tetrahedron Lett. 1996, 37, 7075-7078.
21. Yajima, A.; Saitou, F.; Sekimoto, M.; Maetoko, S.; Yabuta, G. Tetrahedron Lett. 2003, 44, 6915-6918.
22. (a) Anet, E. F. L. J. Aust. J. Chem. 1970, 23, 2101-2108.
23. (b) Hegedus, L. S.; Varaprath, S. Organometallics 1982, 1, 259-263.