A formal [3 + 3] cycloaddition reaction. Improved reactivity using α,β-unsaturated iminium salts and evidence for reversibility of 6π-electron electrocyclic ring closure of 1-oxatrienes

Journal of Organic Chemistry

Volumn 68, Issue 5, 2003, Pages 1729-1735

  Shen, Hong C ^a   Wang, Jiashi ^a   Cole, Kevin P ^a   McLaughlin, Michael J ^a   Morgan, Christopher D ^a   Douglas, Christopher J ^a   Hsung, Richard P ^a   Coverdale, Heather A ^a   Gerasyuto, Aleksey I ^a   Hahn, Juliet M ^a   Liu, Jia ^a   Sklenicka, Heather M ^a   Wei, Lin Li ^a   Zehnder, Luke R ^a   Zificsak, Craig A ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOADDITION REACTIONS;

CONDENSATION; ELECTRONS; KETONES; SALTS;

ADDITION REACTIONS;

1 OXATRIENE DERIVATIVE; 1,3 DIKETONE; 2 PYRONE DERIVATIVE; 4 HYDROXY 2 PYRANONE DERIVATIVE; DIKETONE; IMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CYCLOADDITION; POLYMERIZATION; REACTION ANALYSIS; RING CLOSING METATHESIS; STEREOCHEMISTRY;

ALKENES; CATALYSIS; CHEMISTRY, ORGANIC; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; IMINES; INDICATORS AND REAGENTS; KETONES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PYRANS; PYRONES; SALTS; STEREOISOMERISM;

EID: 0037424327     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020688t     Document Type: Article

References (94)

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53. Tomoda, H.; Tabata, N.; Yang, D. J.; Namatame, I.; Tanaka, H.; Õmura, S.; Kaneko, T. J. Antibiot. 1996, 49, 292. (b) b) Obata, R.; Sunazuka, T.; Li, Z. R.; Tian, Z. M.; Harigava, Y.; Tabata, N.; Tomoda, H.; Õmur, S. J. Antibiotics 1996, 49, 1133. For total synthesis of pyripyropene A and E, see: (c) Smith, A. B., III; Kinsho, T.; Sunazuka, T.; Õmura, S. Tetrahedron Lett. 1996, 37, 6461. (d) Nagamitsu, T.; Sunazuka, T.; Obata, R.; Tomoda, H.; Tanaka, H.; Harigaya, Y.; Õmura, S.; Smith, A. B., III. J. Org. Chem. 1995, 60, 8126. For synthesis of a related natural product GERI-BP001, see: (d) Parker, K. A.; Resnick, L. J. Org. Chem. 1995, 60, 5726. For a biosynthesis of pyripyropene A, see: (e) Tomoda, H.; Tabata, N.; Nakata, Y.; Nishida, H.; Kaneko, T.; Obata, R.; Sunzazuka, T.; Õmura, S. J. Org. Chem. 1996, 61, 882. Obata, R.; Sunazuka, T.; Tian, Z.; Tomoda, H.; Harigaya, Y.; Õmura, S.; Smith, A. B., III. Chem. Lett. 1997, 935.
54. Tomoda, H.; Tabata, N.; Yang, D. J.; Namatame, I.; Tanaka, H.; Õmura, S.; Kaneko, T. J. Antibiot. 1996, 49, 292. (b) b) Obata, R.; Sunazuka, T.; Li, Z. R.; Tian, Z. M.; Harigava, Y.; Tabata, N.; Tomoda, H.; Õmur, S. J. Antibiotics 1996, 49, 1133. For total synthesis of pyripyropene A and E, see: (c) Smith, A. B., III; Kinsho, T.; Sunazuka, T.; Õmura, S. Tetrahedron Lett. 1996, 37, 6461. (d) Nagamitsu, T.; Sunazuka, T.; Obata, R.; Tomoda, H.; Tanaka, H.; Harigaya, Y.; Õmura, S.; Smith, A. B., III. J. Org. Chem. 1995, 60, 8126. For synthesis of a related natural product GERI-BP001, see: (d) Parker, K. A.; Resnick, L. J. Org. Chem. 1995, 60, 5726. For a biosynthesis of pyripyropene A, see: (e) Tomoda, H.; Tabata, N.; Nakata, Y.; Nishida, H.; Kaneko, T.; Obata, R.; Sunzazuka, T.; Õmura, S. J. Org. Chem. 1996, 61, 882. Obata, R.; Sunazuka, T.; Tian, Z.; Tomoda, H.; Harigaya, Y.; Õmura, S.; Smith, A. B., III. Chem. Lett. 1997, 935.
55. Tomoda, H.; Tabata, N.; Yang, D. J.; Namatame, I.; Tanaka, H.; Õmura, S.; Kaneko, T. J. Antibiot. 1996, 49, 292. (b) b) Obata, R.; Sunazuka, T.; Li, Z. R.; Tian, Z. M.; Harigava, Y.; Tabata, N.; Tomoda, H.; Õmur, S. J. Antibiotics 1996, 49, 1133. For total synthesis of pyripyropene A and E, see: (c) Smith, A. B., III; Kinsho, T.; Sunazuka, T.; Õmura, S. Tetrahedron Lett. 1996, 37, 6461. (d) Nagamitsu, T.; Sunazuka, T.; Obata, R.; Tomoda, H.; Tanaka, H.; Harigaya, Y.; Õmura, S.; Smith, A. B., III. J. Org. Chem. 1995, 60, 8126. For synthesis of a related natural product GERI-BP001, see: (d) Parker, K. A.; Resnick, L. J. Org. Chem. 1995, 60, 5726. For a biosynthesis of pyripyropene A, see: (e) Tomoda, H.; Tabata, N.; Nakata, Y.; Nishida, H.; Kaneko, T.; Obata, R.; Sunzazuka, T.; Õmura, S. J. Org. Chem. 1996, 61, 882. Obata, R.; Sunazuka, T.; Tian, Z.; Tomoda, H.; Harigaya, Y.; Õmura, S.; Smith, A. B., III. Chem. Lett. 1997, 935.
56. a) Shu, Y.-Z.; Ye, Q.; Li, H.; Kadow, K. F.; Hussain, R. A.; Huang, S.; Gustavson, D. R.; Lowe, S. E.; Chang, L. P..; Pirnik, D. M.; Kodukula, K. Bioorg. Med. Chem. Lett. 1997, 17, 22295.
57. (b) Organ, M. G.; Bratovanov, S. Tetrahedron Lett. 2000, 41, 6945.
58. John, V.; Lieberburg, I.; Thorsett, E. D. Ann. Rep. Med. Chem. 1993, 28, 197.
59. For our earlier efforts in total synthesis arisugacin A, see the following references. 4-Pyrone Diels-Alder route: (a) Hsung, R. P. J. Org. Chem. 1997, 62, 7904. (b) Granum, K. G.; Merkel, G.; Mulder, J. A.; Debbins, S. A.; Hsung, R. P. Tetrahedron Lett. 1998, 39, 9597. (c) Hsung, R. P. Heterocycles 1998, 48, 421. (d) Hsung R. P.; Zificsak, C. A.; Wei, L.-L.; Zehnder, L. R.; Park, F.; Kim, M.; Tran, T.-T. T. J. Org. Chem. 1999, 64, 8736. (e) Degen, S. J.; Mueller, K. L.; Shen, H. C.; Mulder, J. A.; Golding, G. M.; Wei, L.-L.; Zificsak, C. A.; Neeno-Eckwall, A.; Hsung, R. P. Bioorg. Med. Chem. Lett. 1999, 973, 3. For an acid condensation approach: (f) Zehnder, L. R.; Dahl, J. W.; Hsung, R. P. Tetrahedron Lett. 2000, 41, 1901.
60. For our earlier efforts in total synthesis arisugacin A, see the following references. 4-Pyrone Diels-Alder route: (a) Hsung, R. P. J. Org. Chem. 1997, 62, 7904. (b) Granum, K. G.; Merkel, G.; Mulder, J. A.; Debbins, S. A.; Hsung, R. P. Tetrahedron Lett. 1998, 39, 9597. (c) Hsung, R. P. Heterocycles 1998, 48, 421. (d) Hsung R. P.; Zificsak, C. A.; Wei, L.-L.; Zehnder, L. R.; Park, F.; Kim, M.; Tran, T.-T. T. J. Org. Chem. 1999, 64, 8736. (e) Degen, S. J.; Mueller, K. L.; Shen, H. C.; Mulder, J. A.; Golding, G. M.; Wei, L.-L.; Zificsak, C. A.; Neeno-Eckwall, A.; Hsung, R. P. Bioorg. Med. Chem. Lett. 1999, 973, 3. For an acid condensation approach: (f) Zehnder, L. R.; Dahl, J. W.; Hsung, R. P. Tetrahedron Lett. 2000, 41, 1901.
61. For our earlier efforts in total synthesis arisugacin A, see the following references. 4-Pyrone Diels-Alder route: (a) Hsung, R. P. J. Org. Chem. 1997, 62, 7904. (b) Granum, K. G.; Merkel, G.; Mulder, J. A.; Debbins, S. A.; Hsung, R. P. Tetrahedron Lett. 1998, 39, 9597. (c) Hsung, R. P. Heterocycles 1998, 48, 421. (d) Hsung R. P.; Zificsak, C. A.; Wei, L.-L.; Zehnder, L. R.; Park, F.; Kim, M.; Tran, T.-T. T. J. Org. Chem. 1999, 64, 8736. (e) Degen, S. J.; Mueller, K. L.; Shen, H. C.; Mulder, J. A.; Golding, G. M.; Wei, L.-L.; Zificsak, C. A.; Neeno-Eckwall, A.; Hsung, R. P. Bioorg. Med. Chem. Lett. 1999, 973, 3. For an acid condensation approach: (f) Zehnder, L. R.; Dahl, J. W.; Hsung, R. P. Tetrahedron Lett. 2000, 41, 1901.
62. For our earlier efforts in total synthesis arisugacin A, see the following references. 4-Pyrone Diels-Alder route: (a) Hsung, R. P. J. Org. Chem. 1997, 62, 7904. (b) Granum, K. G.; Merkel, G.; Mulder, J. A.; Debbins, S. A.; Hsung, R. P. Tetrahedron Lett. 1998, 39, 9597. (c) Hsung, R. P. Heterocycles 1998, 48, 421. (d) Hsung R. P.; Zificsak, C. A.; Wei, L.-L.; Zehnder, L. R.; Park, F.; Kim, M.; Tran, T.-T. T. J. Org. Chem. 1999, 64, 8736. (e) Degen, S. J.; Mueller, K. L.; Shen, H. C.; Mulder, J. A.; Golding, G. M.; Wei, L.-L.; Zificsak, C. A.; Neeno-Eckwall, A.; Hsung, R. P. Bioorg. Med. Chem. Lett. 1999, 973, 3. For an acid condensation approach: (f) Zehnder, L. R.; Dahl, J. W.; Hsung, R. P. Tetrahedron Lett. 2000, 41, 1901.
63. For our earlier efforts in total synthesis arisugacin A, see the following references. 4-Pyrone Diels-Alder route: (a) Hsung, R. P. J. Org. Chem. 1997, 62, 7904. (b) Granum, K. G.; Merkel, G.; Mulder, J. A.; Debbins, S. A.; Hsung, R. P. Tetrahedron Lett. 1998, 39, 9597. (c) Hsung, R. P. Heterocycles 1998, 48, 421. (d) Hsung R. P.; Zificsak, C. A.; Wei, L.-L.; Zehnder, L. R.; Park, F.; Kim, M.; Tran, T.-T. T. J. Org. Chem. 1999, 64, 8736. (e) Degen, S. J.; Mueller, K. L.; Shen, H. C.; Mulder, J. A.; Golding, G. M.; Wei, L.-L.; Zificsak, C. A.; Neeno-Eckwall, A.; Hsung, R. P. Bioorg. Med. Chem. Lett. 1999, 973, 3. For an acid condensation approach: (f) Zehnder, L. R.; Dahl, J. W.; Hsung, R. P. Tetrahedron Lett. 2000, 41, 1901.
64. For our earlier efforts in total synthesis arisugacin A, see the following references. 4-Pyrone Diels-Alder route: (a) Hsung, R. P. J. Org. Chem. 1997, 62, 7904. (b) Granum, K. G.; Merkel, G.; Mulder, J. A.; Debbins, S. A.; Hsung, R. P. Tetrahedron Lett. 1998, 39, 9597. (c) Hsung, R. P. Heterocycles 1998, 48, 421. (d) Hsung R. P.; Zificsak, C. A.; Wei, L.-L.; Zehnder, L. R.; Park, F.; Kim, M.; Tran, T.-T. T. J. Org. Chem. 1999, 64, 8736. (e) Degen, S. J.; Mueller, K. L.; Shen, H. C.; Mulder, J. A.; Golding, G. M.; Wei, L.-L.; Zificsak, C. A.; Neeno-Eckwall, A.; Hsung, R. P. Bioorg. Med. Chem. Lett. 1999, 973, 3. For an acid condensation approach: (f) Zehnder, L. R.; Dahl, J. W.; Hsung, R. P. Tetrahedron Lett. 2000, 41, 1901.
65. For our formal [3 + 3] cycloaddition approach, see: Zehnder, L. R.; Hsung, R. P.; Wang, J.-S.; Golding, G. M. Angew. Chem., Int. Ed. 2000, 39, 3876.
66. For an identical route, see: Handa, M.; Sunazuka, T.; Nagai, K.; Kimura, R.; Shirahata, T.; Tian, Z. M.; Otoguro, K.; Harigaya, Y.; Õmura, S. J. Antibiot. 2001, 54, 382.
67. Jonassohn, M.; Sterner, O.; Anke, H. Tetrahedron 1996, 52, 1473.
68. Hua, D. H.; Chen, Y.; Sin, H.-S.; Maroto, M. J.; Robinson, P. D.; Newell, S. W.; Perchellet, E. M.; Ladesich, J. B.; Freeman, J. A.; Perchellet, J.-P.; Chiang, P. K. J. Org. Chem. 1997, 62, 6888.
69. Hsung, R. P.; Shen, H. C.; Douglas, C. J.; Morgan, C. D.; Degen, S. J.; Yao, L. J. J. Org. Chem. 1999, 64, 690. For preliminary communications on the formal [3 + 3] cycloaddition approach, see: Shen, H. C.; Degen, S. J.; Mulder, J. A.; Hsung, R. P.; Douglas C. J.; Golding, G. M.; Johnson, E. W.; Mathias, D. S.; Morgan, C. D.; Mueller, K. L.; Shih, R. A. Abstract No. ORGN-664, 216th ACS National Meeting, Boston, MA, Fall 1998.
70. Hsung, R. P.; Shen, H. C.; Douglas, C. J.; Morgan, C. D.; Degen, S. J.; Yao, L. J. J. Org. Chem. 1999, 64, 690. For preliminary communications on the formal [3 + 3] cycloaddition approach, see: Shen, H. C.; Degen, S. J.; Mulder, J. A.; Hsung, R. P.; Douglas C. J.; Golding, G. M.; Johnson, E. W.; Mathias, D. S.; Morgan, C. D.; Mueller, K. L.; Shih, R. A. Abstract No. ORGN-664, 216th ACS National Meeting, Boston, MA, Fall 1998.
71. For a recent citation in support the usage of α,β-unsaturated iminium salts, see: Cravotto, G.; Nano, G. M.; Tagliapietra, S. Synthesis 2001, 49.
72. For recent related studies in this area: Hua, D. H.; Chen, Y.; Sin, H.-S.; Robinson, P. D.; Meyers, C. Y.; Perchellet, E. M.; Perchellet, J.-P.; Chiang, P. K.; Biellmann, J.-P. Acta Crystallogr. 1999, C55, 1698. (b) P. Benovsky, G. A. Stephenson, J. R. Stille, J. Am. Chem. Soc. 1998, 120, 2493. (c) Moorhoff, C. M. Synthesis, 1997, 685. (d) Krasnaya, Z. A.; Bogdanov, V. S.; Burova, S. A.; Smirnova, Y. V. Russ. Chem. 1995, 44, 2118. (e) Heber, D.; Berghaus, Th. J. Heterocycl. Chem. 1994, 31, 1353. (f) Paulvannan,; K.; Stille, J. R. Tetrahedron Lett. 1993, 34. 6677. (g) Appendino, G.; Cravotto, G.; Tagliapietra, S.; Nano, G. M.; Palmisano, G. Helv. Chim. Acta 1990, 73, 1865.
73. For recent related studies in this area: Hua, D. H.; Chen, Y.; Sin, H.-S.; Robinson, P. D.; Meyers, C. Y.; Perchellet, E. M.; Perchellet, J.-P.; Chiang, P. K.; Biellmann, J.-P. Acta Crystallogr. 1999, C55, 1698. (b) P. Benovsky, G. A. Stephenson, J. R. Stille, J. Am. Chem. Soc. 1998, 120, 2493. (c) Moorhoff, C. M. Synthesis, 1997, 685. (d) Krasnaya, Z. A.; Bogdanov, V. S.; Burova, S. A.; Smirnova, Y. V. Russ. Chem. 1995, 44, 2118. (e) Heber, D.; Berghaus, Th. J. Heterocycl. Chem. 1994, 31, 1353. (f) Paulvannan,; K.; Stille, J. R. Tetrahedron Lett. 1993, 34. 6677. (g) Appendino, G.; Cravotto, G.; Tagliapietra, S.; Nano, G. M.; Palmisano, G. Helv. Chim. Acta 1990, 73, 1865.
74. For recent related studies in this area: Hua, D. H.; Chen, Y.; Sin, H.-S.; Robinson, P. D.; Meyers, C. Y.; Perchellet, E. M.; Perchellet, J.-P.; Chiang, P. K.; Biellmann, J.-P. Acta Crystallogr. 1999, C55, 1698. (b) P. Benovsky, G. A. Stephenson, J. R. Stille, J. Am. Chem. Soc. 1998, 120, 2493. (c) Moorhoff, C. M. Synthesis, 1997, 685. (d) Krasnaya, Z. A.; Bogdanov, V. S.; Burova, S. A.; Smirnova, Y. V. Russ. Chem. 1995, 44, 2118. (e) Heber, D.; Berghaus, Th. J. Heterocycl. Chem. 1994, 31, 1353. (f) Paulvannan,; K.; Stille, J. R. Tetrahedron Lett. 1993, 34. 6677. (g) Appendino, G.; Cravotto, G.; Tagliapietra, S.; Nano, G. M.; Palmisano, G. Helv. Chim. Acta 1990, 73, 1865.
75. For recent related studies in this area: Hua, D. H.; Chen, Y.; Sin, H.-S.; Robinson, P. D.; Meyers, C. Y.; Perchellet, E. M.; Perchellet, J.-P.; Chiang, P. K.; Biellmann, J.-P. Acta Crystallogr. 1999, C55, 1698. (b) P. Benovsky, G. A. Stephenson, J. R. Stille, J. Am. Chem. Soc. 1998, 120, 2493. (c) Moorhoff, C. M. Synthesis, 1997, 685. (d) Krasnaya, Z. A.; Bogdanov, V. S.; Burova, S. A.; Smirnova, Y. V. Russ. Chem. 1995, 44, 2118. (e) Heber, D.; Berghaus, Th. J. Heterocycl. Chem. 1994, 31, 1353. (f) Paulvannan,; K.; Stille, J. R. Tetrahedron Lett. 1993, 34. 6677. (g) Appendino, G.; Cravotto, G.; Tagliapietra, S.; Nano, G. M.; Palmisano, G. Helv. Chim. Acta 1990, 73, 1865.
76. For recent related studies in this area: Hua, D. H.; Chen, Y.; Sin, H.-S.; Robinson, P. D.; Meyers, C. Y.; Perchellet, E. M.; Perchellet, J.-P.; Chiang, P. K.; Biellmann, J.-P. Acta Crystallogr. 1999, C55, 1698. (b) P. Benovsky, G. A. Stephenson, J. R. Stille, J. Am. Chem. Soc. 1998, 120, 2493. (c) Moorhoff, C. M. Synthesis, 1997, 685. (d) Krasnaya, Z. A.; Bogdanov, V. S.; Burova, S. A.; Smirnova, Y. V. Russ. Chem. 1995, 44, 2118. (e) Heber, D.; Berghaus, Th. J. Heterocycl. Chem. 1994, 31, 1353. (f) Paulvannan,; K.; Stille, J. R. Tetrahedron Lett. 1993, 34. 6677. (g) Appendino, G.; Cravotto, G.; Tagliapietra, S.; Nano, G. M.; Palmisano, G. Helv. Chim. Acta 1990, 73, 1865.
77. For recent related studies in this area: Hua, D. H.; Chen, Y.; Sin, H.-S.; Robinson, P. D.; Meyers, C. Y.; Perchellet, E. M.; Perchellet, J.-P.; Chiang, P. K.; Biellmann, J.-P. Acta Crystallogr. 1999, C55, 1698. (b) P. Benovsky, G. A. Stephenson, J. R. Stille, J. Am. Chem. Soc. 1998, 120, 2493. (c) Moorhoff, C. M. Synthesis, 1997, 685. (d) Krasnaya, Z. A.; Bogdanov, V. S.; Burova, S. A.; Smirnova, Y. V. Russ. Chem. 1995, 44, 2118. (e) Heber, D.; Berghaus, Th. J. Heterocycl. Chem. 1994, 31, 1353. (f) Paulvannan,; K.; Stille, J. R. Tetrahedron Lett. 1993, 34. 6677. (g) Appendino, G.; Cravotto, G.; Tagliapietra, S.; Nano, G. M.; Palmisano, G. Helv. Chim. Acta 1990, 73, 1865.
78. For recent related studies in this area: Hua, D. H.; Chen, Y.; Sin, H.-S.; Robinson, P. D.; Meyers, C. Y.; Perchellet, E. M.; Perchellet, J.-P.; Chiang, P. K.; Biellmann, J.-P. Acta Crystallogr. 1999, C55, 1698. (b) P. Benovsky, G. A. Stephenson, J. R. Stille, J. Am. Chem. Soc. 1998, 120, 2493. (c) Moorhoff, C. M. Synthesis, 1997, 685. (d) Krasnaya, Z. A.; Bogdanov, V. S.; Burova, S. A.; Smirnova, Y. V. Russ. Chem. 1995, 44, 2118. (e) Heber, D.; Berghaus, Th. J. Heterocycl. Chem. 1994, 31, 1353. (f) Paulvannan,; K.; Stille, J. R. Tetrahedron Lett. 1993, 34. 6677. (g) Appendino, G.; Cravotto, G.; Tagliapietra, S.; Nano, G. M.; Palmisano, G. Helv. Chim. Acta 1990, 73, 1865.
79. Douglas C. J.; Sklenicka, H. M.; Shen, H. C.; Golding, G. M.; Mathias, D. S.; Degen, S. J.; Morgan, C. D.; Shih, R. A.; Mueller, K. L.; Seurer, L. M.; Johnson, E. W.; Hsung, R. P. Tetrahedron 1999, 55, 13683.
80. 1H NMR spectra.
81. For earlier studies, see: a) Schuda, P. F.; Price, W. A. J. Org. Chem. 1987, 52, 1972.
82. Tietze, L. F.; v. Kiedrowski, G.; Berger, B. Synthesis 1982, 683.
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84. Stevenson, R.; Weber, J. V. J. Nat. Prod. 1988, 51, 1215.
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86. The compound 57 has been made before via a Diels-Alder reaction of DMAD with dioxolane of 4-oxo-4,5,6,7-tetrahydrobenzo[b]-furans. See: (a) Tochtermann, W.; Heinke, T. Tetrahedron Lett. 1978, 19, 2145. (b) Tochtermann, W.; Heinke, K. Chem Ber. 1980, 113, 3249.
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92. (a) Cole, K. P.; Hsung, R. P. Tetrahedron Lett. 2002, 43, 8791.
93. (b) Wang, J.; Cole, K. P.; Wei, L. L.; Zehnder, L. R.; Hsung, R. P. Tetrahedron Lett. 2002, 43, 3337.
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