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Volumn 70, Issue 9, 2005, Pages 3745-3748

Enantioselective total synthesis of (-)-curcuquinone via regioselective chromium-mediated benzannulation

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHROMIUM; ETHERS; MARINE BIOLOGY; SYNTHESIS (CHEMICAL);

EID: 17744400729     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0500939     Document Type: Article
Times cited : (27)

References (33)
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    • (b) (+)-Curcuphenol has been isolated from the Jamaican sponge, Didiscus oxeata.
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    • For total syntheses of racemic curcuquinone, see: (a) Sánchez, I. H.; Lemini, C.; Joseph-Nathan, P. J. Org. Chem. 1981, 46, 4666-4667. (b) Ono, M.; Yamamoto, Y.; Todoriki, R.; Akita, H. Heterocycles 1994, 37, 181-185. (c) Ono, M.; Yamamoto, Y.; Akita, H. Chem. Pharm. Bull. 1995, 43, 553. (d) Vyryan, J. R.; Loitz, C.; Looper, R. E.; Mattingly, C. S.; Peterson, E. A.; Staben, S. T. J. Org. Chem. 2004, 6, 2461-2468.
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    • For total syntheses of racemic curcuquinone, see: (a) Sánchez, I. H.; Lemini, C.; Joseph-Nathan, P. J. Org. Chem. 1981, 46, 4666-4667. (b) Ono, M.; Yamamoto, Y.; Todoriki, R.; Akita, H. Heterocycles 1994, 37, 181-185. (c) Ono, M.; Yamamoto, Y.; Akita, H. Chem. Pharm. Bull. 1995, 43, 553. (d) Vyryan, J. R.; Loitz, C.; Looper, R. E.; Mattingly, C. S.; Peterson, E. A.; Staben, S. T. J. Org. Chem. 2004, 6, 2461-2468.
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    • For a recent review, see: (b) Minatti, A.; Dötz, K. H. In Topics in Organometallic Chemistry; Dötz, K. H., Ed.; Springer: Heidelberg, Germany, 2004; pp 123-157. (c) de Meijere, A.; Schirmer, H.; Duetsch, M. Angew. Chem., Int. Ed. 2000, 39, 3964-4002. (d) Dötz, K. H.; Tomuschat, P. Chem. Soc. Rev. 1999, 28, 187-198. For mechanistic details, see: (e) Wulff, W. D.; Bax, B. M.; Brandvold, T. A.; Chan, K. S.; Gilbert, A. M.; Hsung, R. P.; Mitchell, J.; Clardy, J. Organometallics 1994, 13, 102-126. (f) Barluenga, J.; Aznar, F.; Gutiérrez, I.; Martín, A.; García-Granda, S.; Llorca-Baragano, M. A. J. Am. Chem. Soc. 2000, 122, 1314-1342.
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    • note
    • 3.
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    • note
    • Racemic aldehyde 7 is commercially available.
  • 31
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    • For the synthesis of racemic 3,7-dimethyl-6-octene-1-yne 3, starting from racemic aldehyde 7, see: (a) Corey, E. J.; Fuchs, P. L. Tetrahedron. Lett. 1972, 36, 3769-3772. (b) Snider, B. B.; Killinger, T. A. J. Org. Chem. 1978, 43, 2161-2164.
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    • For the synthesis of racemic 3,7-dimethyl-6-octene-1-yne 3, starting from racemic aldehyde 7, see: (a) Corey, E. J.; Fuchs, P. L. Tetrahedron. Lett. 1972, 36, 3769-3772. (b) Snider, B. B.; Killinger, T. A. J. Org. Chem. 1978, 43, 2161-2164.
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    • note
    • Attempts to determine the enantiomeric excess of the natural product 1 did not meet with success as enantiomers of curcuquinone could not be separated on HPLC employing standard Chiralcel OD, OG, OB, Chiralpak AD, AS columns.


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