Total syntheses of (±)-deethylibophyllidine using a crisscross annulation: Ring cleavage of octahydroindolo[2,3-α]quinolizines followed by tandem cyclizations of octahydroazecino[5,4-b]indoles

Journal of Organic Chemistry

Volumn 63, Issue 21, 1998, Pages 7338-7347

  Bonjoch, Josep ^a   Fernàndez, Joan Carles ^a   Vails, Nativitat ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0013601608     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980909o     Document Type: Article

References (97)

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70. (a) Prior syntheses of (±)-deethylibophyllidine: refs 4a, 5a, 6a, and 7. (b) For a preliminary account of this part of the work, see: Fernàndez, J. C.; Vails, N.; Bosch, J.; Bonjoch, J. J. Chem. Soc., Chem. Commun. 1995, 2317-2318.
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75. 3, LDA] as described in the Supporting Information.
76. Synthesized from cither Szántay or Kuehne protocol: (a) Blasko, G.; Honty, K; Novak, L.; Szantay, C. Acta Chim. Acad. Sei. Hung. 1979,99, 35-41.
77. (b) Kuehne, M. E.; Muth, R. S. J. Org. Chem. 1991, 56, 2701-2712.
78. For conformational analysis of 2-substituted octahydroindolo[2,3-a]quinolizines, see: Lounasmaa, M.; Jokela, R. Tetrahedron 1989, 45, 3975-3991.
79. The NMR spectra of all octahydroazecinoindoles synthesized in this work are very complicated due to the conformational flexibility of medium sized rings and the duplicity of signals caused by the restricted rotation of the carbamatc bond. For a conformational analysis of simple octahydroazecino[5,4-6]indoles, see: Bonjoch, J.; Fernàndez, J.-C.; Vails, N. Eur. J. Org. Chem., submitted to be published.
80. Dadson, B. A.; Harley-Mason, J. J. Chem. Soc., Chem. Commun. 1969, 665.
81. In one run with longer reaction times (24 h), ketone 16 was formed.
82. For conversion of nitriles to methyl esters, via imidates, see: (a) Mandai, A. N.; Raychaudhuri, S. R.; Chatterjee, A. Synthesis 1983, 727-729.
83. (b) Brussee, J.; Loos, W. T.; Kruse, C. G.; Van Der Gen, A. Tetrahedron 1990, 46, 979-986.
84. For an alkaloid related to 19 with the same stability under hydrolysis, see: Nuzillard, J.-M.; Thépenier, P.; Jacquier, M.-J.; Massiot, G.; Le Men-Olivier, L.; Delaude, C. Phytochemistry 1996,43, 897-902.
85. The removal of the benzyloxycarbonyl group in 22 by means of hydrogenation was reluctant and the secondary amine 23 was only isolated in 35% yield (no other reagents were tested to attempt this decarbamation).
86. Ibophyllidine and 20-epiibophyllidine: Husson, H.-P.; Jacquemin, H.; Kan, S.-K; Lounasmaa, M. Tetrahedron Lett. 1980, 21, 55-58.
87. Bonjoch, J.; Fernandez, J.-C.; Terricabras, D.; Vails, N. Tetrahedron 1997, 53, 9407-9414.
88. For the stereoselectivity in the preparation of indolo[2,3-a]quinolizidine M,-metho salts and NMR data of these compounds, see: Lounasmaa, M.; Tamminen, T. Heterocydes 1991, 32, 1527-1535.
89. When the same reaction was carried out with 7b a mixture of 25b-l and 25b-2 was obtained (6:1 ratio, 89% overall yield, see Supporting Information).
90. To obtain a pure indolo derivative 26, the crude reaction' mixture, in which a dihydroindole derivative appeared, was kept in an oxygen atmosphere in order to reoxidize the over-reduced product.
91. Attempts to form the carbamate from the unprotected indole 26 operating with several chloroformâtes gave lower yields, the best result being with phenyl chloroformate, which gave carbamate 27 in 36% yield.
92. The same compound 30 was isolated in 33% overall yield when allyl chloroformate 29c was treated initially with Pd(PPh3)4/AcOH, Bu3SnH/CH2Cl2, and then with l N aqeous HC1.
93. Accompanied by a low percentatge of 31b and other isomers, all of them synthetically useful.
94. For some examples of steric hindrance in dealkylation processes via carbamates, see: (a) Torisawa, Y.; Nakagawa, M.; Hosaka, T.; Tanabe, K.; Lai, Z.; Ogata, K.; Nakata, T.; Oishi, T.; Hino, T. J. Org. Chem. 1992,57,5741-5747.
95. (b) Tidwell, J. H.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11797-11810.
96. As occurs in the 20-epiibophyllidine syntheses,41'5 the stereoselectivity observed in this cyclization can be ascribed to selective addition of the indole to the iminium salt intermediate of the D ring on the side which is not shielded by the ethyl substituent.
97. It has been noted that our early strategy7 did not allow access to these alkaloids either: Bonjoch, J.; Catena, J.; Terricabras, D.; Fernàndez, J.-C.; López-Canet, M.; Vails, N. Tetrahedron: Asymmetry 1997, 8, 3143-3151.