Origins of selectivity in pericyclic reaction cascades for the synthesis of gambogin and lateriflorone

Organic Letters

Volumn 8, Issue 14, 2006, Pages 2989-2992

  Hayden, Amy E ^a   Xu, Hao ^b   Nicolaou, K C ^b,c   Houk, K N ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BRIDGED COMPOUND; GAMBOGIN; LATERIFLORONE; POLYCYCLIC HYDROCARBON; SPIRO COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALKENES; BRIDGED COMPOUNDS; CRYSTALLOGRAPHY, X-RAY; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; POLYCYCLIC COMPOUNDS; SPIRO COMPOUNDS;

EID: 33746646775     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060917o     Document Type: Article

References (11)

1. Asano, J.; Chiba, K.; Tada, M.; Yoshii, T. Phytochemistry 1996, 41, 815.
2. Kosela, S.; Gao, S.-G.; Wu, X.-H.; Vittal, J. J.; Sukri, T.; Goh, S.-H.; Sim, K.-Y. Tetrahedron Lett. 1999, 40, 157.
3. Nicolaou, K. C.; Li, J. Angew. Chem., Int. Ed. 2003, 42, 4264.
4. Nicolaou, K. C.; Xu, H.; Wartmann, M. Angew. Chem., Int. Ed. 2005, 44, 756.
5. Nicolaou, K. C.; Sasmal, P. K.; Xu, H.; Namoto, K.; Ritzen, A. Angew Chem., Int. Ed. 2003, 42, 4225.
6. Nicolaou, K. C.; Sasmal, P. K.; Xu, H. J. Am. Chem. Soc. 2004, 126, 5493.
7. Tisdale, E. J.; Li, H.; Vong, B. G.; Kim, S. H.; Theodorakis, E. A. Org Lett. 2003, 5, 1491.
8. Tisdale, E. J.; Vong, B. G.; Li, H.; Kim, S. H.; Chowdhury, C.; Theodorakis, E. A. Tetrahedron 2003, 59, 6873.
9. Tisdale, E. J.; Slobodov, I.; Theodorakis, E. A. Org. Biomol. Chem. 2003, 1, 4418.
10. Tisdale, E. J.; Slobodov, I.; Theodorakis, E. A. PNAS 2004, 101, 12030.
11. Gaussian 03, revision C.02: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K.; Burant, J. C.; Millam, J. M.; Iyengay, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Comperts, R.; Startmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenbuerg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chem, W.; Wong, M. W., Gonzalez, C.; Pople, J. A. Gaussian, Inc.: Wallingford CT, 2004.