A route to Z-enediynes via Pd catalyzed alkyne additions

Tetrahedron Letters

Volumn 39, Issue 36, 1998, Pages 6445-6448

  Trost, Barry M ^a   Hachiya, Iwao ^a   McIntosh, Matthias C ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYLDIALKYNE DERIVATIVE; ALKYNE; ALKYNE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; ISOMERISM; REACTION ANALYSIS;

EID: 0032171506     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01392-6     Document Type: Article

References (20)

1. 1. Leet, J.E.; Schroeder, D.R.; Langley, D.R.; Langley, D.R.; Colson, K.L.; Huang, S.; Klohr, S.E.; Lee, M.S.; Golik, J. Hofstead, S.J.; Doyle, T.W.; Matson, J.A. J. Am. Chem. Soc. 1993, 115, 8432.
2. 2. Edo, K.; Mizugaki, M.; Koide, Y.; Seto, H.; Furihata, K.; Otake, N.; Ishida, N. Tetrahedron Lett. 1985, 26, 331; Edo, K.; Akiyama, Y.; Saito, K.; Mizugaki, M.; Koide, Y.; Ishida, N. J. Antibiot. 1986, 39, 1615; Myers, A.G.; Proteau, P.J.; Handel, T.M. J. Am. Chem. Soc. 1988, 110, 7212. For the synthesis of neocarzinostatin chromophore aglycon, see: Myers, A.G.; Hammond, M.; Wu, Y.; Xiang, J.-N.; Harrington, P.M.; Kuo, E.Y. J. Am. Chem. Soc. 1996, 118, 10006.
3. 2. Edo, K.; Mizugaki, M.; Koide, Y.; Seto, H.; Furihata, K.; Otake, N.; Ishida, N. Tetrahedron Lett. 1985, 26, 331; Edo, K.; Akiyama, Y.; Saito, K.; Mizugaki, M.; Koide, Y.; Ishida, N. J. Antibiot. 1986, 39, 1615; Myers, A.G.; Proteau, P.J.; Handel, T.M. J. Am. Chem. Soc. 1988, 110, 7212. For the synthesis of neocarzinostatin chromophore aglycon, see: Myers, A.G.; Hammond, M.; Wu, Y.; Xiang, J.-N.; Harrington, P.M.; Kuo, E.Y. J. Am. Chem. Soc. 1996, 118, 10006.
4. 2. Edo, K.; Mizugaki, M.; Koide, Y.; Seto, H.; Furihata, K.; Otake, N.; Ishida, N. Tetrahedron Lett. 1985, 26, 331; Edo, K.; Akiyama, Y.; Saito, K.; Mizugaki, M.; Koide, Y.; Ishida, N. J. Antibiot. 1986, 39, 1615; Myers, A.G.; Proteau, P.J.; Handel, T.M. J. Am. Chem. Soc. 1988, 110, 7212. For the synthesis of neocarzinostatin chromophore aglycon, see: Myers, A.G.; Hammond, M.; Wu, Y.; Xiang, J.-N.; Harrington, P.M.; Kuo, E.Y. J. Am. Chem. Soc. 1996, 118, 10006.
5. 2. Edo, K.; Mizugaki, M.; Koide, Y.; Seto, H.; Furihata, K.; Otake, N.; Ishida, N. Tetrahedron Lett. 1985, 26, 331; Edo, K.; Akiyama, Y.; Saito, K.; Mizugaki, M.; Koide, Y.; Ishida, N. J. Antibiot. 1986, 39, 1615; Myers, A.G.; Proteau, P.J.; Handel, T.M. J. Am. Chem. Soc. 1988, 110, 7212. For the synthesis of neocarzinostatin chromophore aglycon, see: Myers, A.G.; Hammond, M.; Wu, Y.; Xiang, J.-N.; Harrington, P.M.; Kuo, E.Y. J. Am. Chem. Soc. 1996, 118, 10006.
6. 3. For reviews, see: Grissom, J.W.; Gunawardena, G.U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453; Wang, K.K. Chem. Rev. 1996, 96, 207; Maier, M.E. Synlett 1995, 13; Nicolaou, K.C., Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387.
7. 3. For reviews, see: Grissom, J.W.; Gunawardena, G.U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453; Wang, K.K. Chem. Rev. 1996, 96, 207; Maier, M.E. Synlett 1995, 13; Nicolaou, K.C., Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387.
8. 3. For reviews, see: Grissom, J.W.; Gunawardena, G.U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453; Wang, K.K. Chem. Rev. 1996, 96, 207; Maier, M.E. Synlett 1995, 13; Nicolaou, K.C., Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387.
9. 3. For reviews, see: Grissom, J.W.; Gunawardena, G.U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453; Wang, K.K. Chem. Rev. 1996, 96, 207; Maier, M.E. Synlett 1995, 13; Nicolaou, K.C., Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387.
10. 4. For some examples, see: Uenishi, J.; Kawahama, R.; Yonemitsu, O.; Tsuji, J. J. Org. Chem. 1996, 61, 5716; Dai, W.-M.; Fong, K.C.; Danjo, H.; Nishimoto, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 779; Alami, M.; Crousse, B.; Linstrumelle, G. Tetrahedron Lett. 1994, 35, 3543; Magirotis, P.A.; Scott, M.E.; Kim, K.D. Tetrahedron Lett. 1992, 32, 6085; Stracker, E.; Zweifel, G. Tetrahedron Lett. 1992, 32, 3329.
11. 4. For some examples, see: Uenishi, J.; Kawahama, R.; Yonemitsu, O.; Tsuji, J. J. Org. Chem. 1996, 61, 5716; Dai, W.-M.; Fong, K.C.; Danjo, H.; Nishimoto, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 779; Alami, M.; Crousse, B.; Linstrumelle, G. Tetrahedron Lett. 1994, 35, 3543; Magirotis, P.A.; Scott, M.E.; Kim, K.D. Tetrahedron Lett. 1992, 32, 6085; Stracker, E.; Zweifel, G. Tetrahedron Lett. 1992, 32, 3329.
12. 4. For some examples, see: Uenishi, J.; Kawahama, R.; Yonemitsu, O.; Tsuji, J. J. Org. Chem. 1996, 61, 5716; Dai, W.-M.; Fong, K.C.; Danjo, H.; Nishimoto, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 779; Alami, M.; Crousse, B.; Linstrumelle, G. Tetrahedron Lett. 1994, 35, 3543; Magirotis, P.A.; Scott, M.E.; Kim, K.D. Tetrahedron Lett. 1992, 32, 6085; Stracker, E.; Zweifel, G. Tetrahedron Lett. 1992, 32, 3329.
13. 4. For some examples, see: Uenishi, J.; Kawahama, R.; Yonemitsu, O.; Tsuji, J. J. Org. Chem. 1996, 61, 5716; Dai, W.-M.; Fong, K.C.; Danjo, H.; Nishimoto, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 779; Alami, M.; Crousse, B.; Linstrumelle, G. Tetrahedron Lett. 1994, 35, 3543; Magirotis, P.A.; Scott, M.E.; Kim, K.D. Tetrahedron Lett. 1992, 32, 6085; Stracker, E.; Zweifel, G. Tetrahedron Lett. 1992, 32, 3329.
14. 4. For some examples, see: Uenishi, J.; Kawahama, R.; Yonemitsu, O.; Tsuji, J. J. Org. Chem. 1996, 61, 5716; Dai, W.-M.; Fong, K.C.; Danjo, H.; Nishimoto, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 779; Alami, M.; Crousse, B.; Linstrumelle, G. Tetrahedron Lett. 1994, 35, 3543; Magirotis, P.A.; Scott, M.E.; Kim, K.D. Tetrahedron Lett. 1992, 32, 6085; Stracker, E.; Zweifel, G. Tetrahedron Lett. 1992, 32, 3329.
15. 5. Trost, B.M.; Sorum, M.T.; Chan, C.; Harms, A.E.; Rühter, G. J. Am. Chem. Soc. 1997, 119, 698; Trost, B.M.; McIntosh, M.C. Tetrahedron Lett. 1997, 38, 3207.
16. 5. Trost, B.M.; Sorum, M.T.; Chan, C.; Harms, A.E.; Rühter, G. J. Am. Chem. Soc. 1997, 119, 698; Trost, B.M.; McIntosh, M.C. Tetrahedron Lett. 1997, 38, 3207.
17. 6. This compound has been fully characterized spectroscopically and the elemental composition established by high resolution mass spectrometry or combustion analysis.
18. 7. Trost, B.M.; McIntosh, M.C. J. Am. Chem. Soc. 1995, 117, 7255.
19. 8. Cf. Barrett, A.G.M.; Barton, D.H.R.; Johnson, G.; Nagubandi, S. Synthesis 1978, 741.
20. 9. Yaw, E.K.; Coward, K. J. Org. Chem. 1990, 55, 3147.