Total synthesis of (S)-(+)-citreofuran by ring closing alkyne metathesis

Journal of Organic Chemistry

Volumn 68, Issue 4, 2003, Pages 1521-1528

  Fürstner, Alois ^a   Castanet, Anne Sophie ^a   Radkowski, Karin ^a   Lehmann, Christian W ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

METATHESIS;

AROMATIZATION; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

AROMATIC HYDROCARBONS;

ALKYNE; CITREOFURAN; DOUBLE STRANDED DNA; MACROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DNA CLEAVAGE; NONHUMAN; RING CLOSING METATHESIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALKYNES; ALTERNARIA; ASCOMYCOTA; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; DNA DAMAGE; FURANS; INDICATORS AND REAGENTS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PENICILLIUM; STEREOISOMERISM; ZEARALENONE;

EID: 0037458905     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026686q     Document Type: Article

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87. 3. While the use of TMSCl as activating agent in 1,2-additions of RMgX to carbonyl compounds seems to be largely unexplored, its accelerating effect on 1,4-additions under "Kharasch conditions" (RMgX + Cu cat.) or with preformed organocuprates as the reagents is well precedented. See the following for leading references and literature cited therein: (a) Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1985, 26, 6015-6018. (b) Nakamura, E.; Matsuzawa, S.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1986, 27, 4029-4032. (c) Linderman, R. J.; Godfrey, A. Tetrahedron Lett. 1986, 27, 4553-4556. (d) Alexakis, A.; Berlan, J.; Besace, Y. Tetrahedron Lett. 1986, 27, 1047-1050. (e) Lipshutz, B. H.; Aue, D. H.; James, B. Tetrahedron Lett. 1996, 37, 8471-8474. (f) Reetz, M. T.; Kindler, A. J. Organomet. Chem. 1995, 502 C5-C7. (g) Yamazaki, T.; Umetani, H.; Kitazume, T. Tetrahedron Lett. 1997, 38, 6705-6708. (h) Bertz, S. H.; Miao, G.; Rossiter, B. E.; Snyder, J. P. J. Am. Chem. Soc. 1995, 117, 11023-11024.
88. 3. While the use of TMSCl as activating agent in 1,2-additions of RMgX to carbonyl compounds seems to be largely unexplored, its accelerating effect on 1,4-additions under "Kharasch conditions" (RMgX + Cu cat.) or with preformed organocuprates as the reagents is well precedented. See the following for leading references and literature cited therein: (a) Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1985, 26, 6015-6018. (b) Nakamura, E.; Matsuzawa, S.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1986, 27, 4029-4032. (c) Linderman, R. J.; Godfrey, A. Tetrahedron Lett. 1986, 27, 4553-4556. (d) Alexakis, A.; Berlan, J.; Besace, Y. Tetrahedron Lett. 1986, 27, 1047-1050. (e) Lipshutz, B. H.; Aue, D. H.; James, B. Tetrahedron Lett. 1996, 37, 8471-8474. (f) Reetz, M. T.; Kindler, A. J. Organomet. Chem. 1995, 502 C5-C7. (g) Yamazaki, T.; Umetani, H.; Kitazume, T. Tetrahedron Lett. 1997, 38, 6705-6708. (h) Bertz, S. H.; Miao, G.; Rossiter, B. E.; Snyder, J. P. J. Am. Chem. Soc. 1995, 117, 11023-11024.
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90. 3. While the use of TMSCl as activating agent in 1,2-additions of RMgX to carbonyl compounds seems to be largely unexplored, its accelerating effect on 1,4-additions under "Kharasch conditions" (RMgX + Cu cat.) or with preformed organocuprates as the reagents is well precedented. See the following for leading references and literature cited therein: (a) Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1985, 26, 6015-6018. (b) Nakamura, E.; Matsuzawa, S.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1986, 27, 4029-4032. (c) Linderman, R. J.; Godfrey, A. Tetrahedron Lett. 1986, 27, 4553-4556. (d) Alexakis, A.; Berlan, J.; Besace, Y. Tetrahedron Lett. 1986, 27, 1047-1050. (e) Lipshutz, B. H.; Aue, D. H.; James, B. Tetrahedron Lett. 1996, 37, 8471-8474. (f) Reetz, M. T.; Kindler, A. J. Organomet. Chem. 1995, 502 C5-C7. (g) Yamazaki, T.; Umetani, H.; Kitazume, T. Tetrahedron Lett. 1997, 38, 6705-6708. (h) Bertz, S. H.; Miao, G.; Rossiter, B. E.; Snyder, J. P. J. Am. Chem. Soc. 1995, 117, 11023-11024.
91. 3. While the use of TMSCl as activating agent in 1,2-additions of RMgX to carbonyl compounds seems to be largely unexplored, its accelerating effect on 1,4-additions under "Kharasch conditions" (RMgX + Cu cat.) or with preformed organocuprates as the reagents is well precedented. See the following for leading references and literature cited therein: (a) Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1985, 26, 6015-6018. (b) Nakamura, E.; Matsuzawa, S.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1986, 27, 4029-4032. (c) Linderman, R. J.; Godfrey, A. Tetrahedron Lett. 1986, 27, 4553-4556. (d) Alexakis, A.; Berlan, J.; Besace, Y. Tetrahedron Lett. 1986, 27, 1047-1050. (e) Lipshutz, B. H.; Aue, D. H.; James, B. Tetrahedron Lett. 1996, 37, 8471-8474. (f) Reetz, M. T.; Kindler, A. J. Organomet. Chem. 1995, 502 C5-C7. (g) Yamazaki, T.; Umetani, H.; Kitazume, T. Tetrahedron Lett. 1997, 38, 6705-6708. (h) Bertz, S. H.; Miao, G.; Rossiter, B. E.; Snyder, J. P. J. Am. Chem. Soc. 1995, 117, 11023-11024.
92. 3. While the use of TMSCl as activating agent in 1,2-additions of RMgX to carbonyl compounds seems to be largely unexplored, its accelerating effect on 1,4-additions under "Kharasch conditions" (RMgX + Cu cat.) or with preformed organocuprates as the reagents is well precedented. See the following for leading references and literature cited therein: (a) Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1985, 26, 6015-6018. (b) Nakamura, E.; Matsuzawa, S.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1986, 27, 4029-4032. (c) Linderman, R. J.; Godfrey, A. Tetrahedron Lett. 1986, 27, 4553-4556. (d) Alexakis, A.; Berlan, J.; Besace, Y. Tetrahedron Lett. 1986, 27, 1047-1050. (e) Lipshutz, B. H.; Aue, D. H.; James, B. Tetrahedron Lett. 1996, 37, 8471-8474. (f) Reetz, M. T.; Kindler, A. J. Organomet. Chem. 1995, 502 C5-C7. (g) Yamazaki, T.; Umetani, H.; Kitazume, T. Tetrahedron Lett. 1997, 38, 6705-6708. (h) Bertz, S. H.; Miao, G.; Rossiter, B. E.; Snyder, J. P. J. Am. Chem. Soc. 1995, 117, 11023-11024.
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