ortho-quinone methides from para-quinones: Total synthesis of rubioncolin B

Journal of the American Chemical Society

Volumn 130, Issue 29, 2008, Pages 9230-9231

  Lumb, Jean Philip ^a   Choong, Kevin C ^a   Trauner, Dirk ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; ACETONE; ALCOHOL DERIVATIVE; ALKADIENE; CARBOXYLIC ACID DERIVATIVE; CHLORIDE; FURAN DERIVATIVE; HYDROQUINONE; QUINONE DERIVATIVE; RUBIONCOLIN B; TRIETHYLAMINE;

ACIDITY; ARTICLE; CYCLIZATION; DENSITY FUNCTIONAL THEORY; DIELS ALDER REACTION; DRUG SYNTHESIS; ENERGY; ESTERIFICATION; LITHIATION; METHYLATION; OXIDATION; PRECURSOR; RESPIRATORY BURST; X RAY ANALYSIS;

DIMERIZATION; FURANS; HYDROQUINONES; INDOLEQUINONES; NAPHTHOLS; PLANT EXTRACTS; POLYENES; QUINONES; RUBIA;

EID: 47749100518     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja803498r     Document Type: Article

References (15)

1. For a comprehensive review, see: Van de Water, R. W.; Pettus, T. R. R. Tetrahedron 2002, 58, 5367-5405.
2. For recent examples in total synthesis, see: Bulger, P. G.; Bagal, S. K.; Marquez, R Nat. Prod. Rep. 2008, 25, 254-297, and references therein.
3. Peter, M. G. Angew. Chem., Int. Ed. Engl. 1989, 28, 555-570.
4. Lumb, J. P.; Trauner, D. Org. Lett. 2005, 7, 5865-5868.
5. A tautomerization/intermolecular cycloaddition has been reported by Nicolaou, K. C.; Lim, Y. H.; Papageorgiou, C. D.; Piper, J. L. Angew. Chem., Int. Ed. 2005, 44, 7917-7921.
6. Itokawa, H.; Ibraheim, Z. Z.; Qiao, Y. F.; Takeya, K. Chem. Pharm. Bull. 1993, 41, 1869-1872, and references therein.
7. Singh, R.; Geetanjali; Chauhan, S. M. S. Chem. Biodiversity 2004, 1, 1241-1264.
8. For the biomimetic synthesis of another member in this family, see: Lumb, J. P.; Trauner, D. J. Am. Chem. Soc. 2005, 127, 2870-2871.
9. Jaguar, version 6.5; Schrödinger, LLC: New York, NY, 2006. See Supporting Information for details.
10. (a) Ciganek, E. J. Am. Chem. Soc. 1981, 103, 6261-6262, and references therein.
11. (b) An intramolecular Diels-Alder addition to a benzofuran has been used in a total synthesis of morphine. Gilbert Stork, private communication.
12. (c) Chen, C. H.; Rao, P. D.; Liao, C. C. J. Am. Chem. Soc. 1998, 120, 13254-13255.
13. (d) Noland, W. E.; Kedrowski, B. L. J. Org. Chem. 1999, 64, 596-603.
14. For a synthesis of quinone 12, see: Barker, D.; Brimble, M. A.; Do, P.; Turner, P. Tetrahedron 2003, 59, 2441-2449.
15. For a similar Sakurai-type allylation, see: Uno, H. J. Org. Chem. 1986, 51, 350-358.