Total synthesis of (+)-xestoquinone using an asymmetric palladium-catalyzed polyene cyclization

Journal of the American Chemical Society

Volumn 118, Issue 44, 1996, Pages 10766-10773

  Maddaford, Shawn P ^a   Andersen, Neil G ^a   Cristofoli, Walter A ^a   Keay, Brian A ^a  

^a UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

POLYKETIDE; UNCLASSIFIED DRUG; XESTOQUINONE;

ARTICLE; CATALYSIS; CHIRALITY; CIRCULAR DICHROISM; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0029799202     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja960807k     Document Type: Article

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71. (b) Siemanowski, W.; Witzel, H. Liebigs. Ann. Chim. 1984, 1731.
72. Heck, R. F. Vinyl Substitutions with Organopalladium Intermediates. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, p 833.
73. (a) Dean, F. M. Adv. Heterocycl. Chem. 1982, 30, 167.
74. (b) Dean, F. M. Adv. Heterocycl. Chem. 1982, 31, 237.
75. Andersen, N. G.; Maddaford, S. P.; Keay, B. A. J. Org. Chem. 1996, 61, 2885.
76. Previously, the anion of 29 was generated by treatment with 1.5 equiv of n-BuLi in the presence of HMPA; see ref 8a.
77. Rigby, J. H.; Hughes, R. C.; Heeg, M. J. J. Am. Chem. Soc. 1995, 117, 7834.
78. For a discussion of the role of silver salts, see: (a) Sato, Y.; Sodeoka, M.; Shibasaki, M. Chem. Lett. 1990, 1953. (b) Sato, Y.; Watanabe, S.; Shibasaki, M. Tetrahedron Lett. 1992, 33, 2589. (c) Sato, Y.; Nukui, S.; Sodeoka, M.; Shibasaki, M. Tetrahedron 1994, 50, 371.
79. For a discussion of the role of silver salts, see: (a) Sato, Y.; Sodeoka, M.; Shibasaki, M. Chem. Lett. 1990, 1953. (b) Sato, Y.; Watanabe, S.; Shibasaki, M. Tetrahedron Lett. 1992, 33, 2589. (c) Sato, Y.; Nukui, S.; Sodeoka, M.; Shibasaki, M. Tetrahedron 1994, 50, 371.
80. For a discussion of the role of silver salts, see: (a) Sato, Y.; Sodeoka, M.; Shibasaki, M. Chem. Lett. 1990, 1953. (b) Sato, Y.; Watanabe, S.; Shibasaki, M. Tetrahedron Lett. 1992, 33, 2589. (c) Sato, Y.; Nukui, S.; Sodeoka, M.; Shibasaki, M. Tetrahedron 1994, 50, 371.
81. Higher asymmetric induction can be achieved when triflates are used as the leaving group in the Heck reaction. This has been ascribed to an increase in the liability of the Pd-OTf bond in the oxidative addition complex and allows bidentate coordination of the chiral ligand; see ref 9b.
82. 6a
83. Young, S. D.; Wiggins, J. M.; Huff, J. R. J. Org. Chem. 1988, 53, 1114.