Synthesis of (-)-haliclonadiamine

Journal of the American Chemical Society

Volumn 119, Issue 1, 1997, Pages 22-26

  Taber, Douglass F ^a   Wang, Yanong ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; HALICLONADIAMINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0031055328     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962162u     Document Type: Article

References (29)

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3. Three enantioselective syntheses of papuamine (2) have been reported; see: (a) Barrett, A. G. M.; Boys, M. L.; Boehm, T. L. J. Chem. Soc., Chem. Commun. 1994, 1881. (b) Weinreb, S. M.; Borzilleri, R. M.; Parvez, M. J. Am. Chem. Soc. 1994, 116, 9789. (c) McDermott, T. S.; Mortlock, A.; Heathcock, C. H. J Org. Chem. 1996, 61, 700. (-)-Haliclonadiamine was prepared as a byproduct in this synthesis of (-)-papuamine.
4. Three enantioselective syntheses of papuamine (2) have been reported; see: (a) Barrett, A. G. M.; Boys, M. L.; Boehm, T. L. J. Chem. Soc., Chem. Commun. 1994, 1881. (b) Weinreb, S. M.; Borzilleri, R. M.; Parvez, M. J. Am. Chem. Soc. 1994, 116, 9789. (c) McDermott, T. S.; Mortlock, A.; Heathcock, C. H. J Org. Chem. 1996, 61, 700. (-)-Haliclonadiamine was prepared as a byproduct in this synthesis of (-)-papuamine.
5. Three enantioselective syntheses of papuamine (2) have been reported; see: (a) Barrett, A. G. M.; Boys, M. L.; Boehm, T. L. J. Chem. Soc., Chem. Commun. 1994, 1881. (b) Weinreb, S. M.; Borzilleri, R. M.; Parvez, M. J. Am. Chem. Soc. 1994, 116, 9789. (c) McDermott, T. S.; Mortlock, A.; Heathcock, C. H. J Org. Chem. 1996, 61, 700. (-)-Haliclonadiamine was prepared as a byproduct in this synthesis of (-)-papuamine.
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11. For further studies of Ru-BINAP-mediated hydrogenation of β-keto esters, see: (a) Cesarotti, E.; Mauri, A.; Pallavicini, M.; Villa, L. Tetrahedron Lett. 1991, 32, 4381. (b) Kitamura, M.; Tokunaga, M.; Ohkuma, T; Noyori, R. Tetrahedron Lett. 1991, 32, 4163. (c) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Org. Chem. 1992, 57, 4053. (d) Taber, D. F.; Silverberg, L. J. Tetrahedron Lett. 1991, 32, 4227. (e) King, S. A.; Thompson, A. S.; King, A. O.; Verhoeven, T. R. J. Org. Chem. 1992, 57, 6689. (f) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144. (g) Genet, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Cano De Andrade, M. C.; Laffitte, J. A. Tetrahedron 1994, 5, 665. (h) Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. (i) Burk, M. J.; Harper, T. G. P.; Kalberg, C. S. J. Am. Chem. Soc. 1995, 117, 4423.
12. For further studies of Ru-BINAP-mediated hydrogenation of β-keto esters, see: (a) Cesarotti, E.; Mauri, A.; Pallavicini, M.; Villa, L. Tetrahedron Lett. 1991, 32, 4381. (b) Kitamura, M.; Tokunaga, M.; Ohkuma, T; Noyori, R. Tetrahedron Lett. 1991, 32, 4163. (c) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Org. Chem. 1992, 57, 4053. (d) Taber, D. F.; Silverberg, L. J. Tetrahedron Lett. 1991, 32, 4227. (e) King, S. A.; Thompson, A. S.; King, A. O.; Verhoeven, T. R. J. Org. Chem. 1992, 57, 6689. (f) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144. (g) Genet, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Cano De Andrade, M. C.; Laffitte, J. A. Tetrahedron 1994, 5, 665. (h) Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. (i) Burk, M. J.; Harper, T. G. P.; Kalberg, C. S. J. Am. Chem. Soc. 1995, 117, 4423.
13. For further studies of Ru-BINAP-mediated hydrogenation of β-keto esters, see: (a) Cesarotti, E.; Mauri, A.; Pallavicini, M.; Villa, L. Tetrahedron Lett. 1991, 32, 4381. (b) Kitamura, M.; Tokunaga, M.; Ohkuma, T; Noyori, R. Tetrahedron Lett. 1991, 32, 4163. (c) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Org. Chem. 1992, 57, 4053. (d) Taber, D. F.; Silverberg, L. J. Tetrahedron Lett. 1991, 32, 4227. (e) King, S. A.; Thompson, A. S.; King, A. O.; Verhoeven, T. R. J. Org. Chem. 1992, 57, 6689. (f) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144. (g) Genet, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Cano De Andrade, M. C.; Laffitte, J. A. Tetrahedron 1994, 5, 665. (h) Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. (i) Burk, M. J.; Harper, T. G. P.; Kalberg, C. S. J. Am. Chem. Soc. 1995, 117, 4423.
14. For further studies of Ru-BINAP-mediated hydrogenation of β-keto esters, see: (a) Cesarotti, E.; Mauri, A.; Pallavicini, M.; Villa, L. Tetrahedron Lett. 1991, 32, 4381. (b) Kitamura, M.; Tokunaga, M.; Ohkuma, T; Noyori, R. Tetrahedron Lett. 1991, 32, 4163. (c) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Org. Chem. 1992, 57, 4053. (d) Taber, D. F.; Silverberg, L. J. Tetrahedron Lett. 1991, 32, 4227. (e) King, S. A.; Thompson, A. S.; King, A. O.; Verhoeven, T. R. J. Org. Chem. 1992, 57, 6689. (f) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144. (g) Genet, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Cano De Andrade, M. C.; Laffitte, J. A. Tetrahedron 1994, 5, 665. (h) Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. (i) Burk, M. J.; Harper, T. G. P.; Kalberg, C. S. J. Am. Chem. Soc. 1995, 117, 4423.
15. For further studies of Ru-BINAP-mediated hydrogenation of β-keto esters, see: (a) Cesarotti, E.; Mauri, A.; Pallavicini, M.; Villa, L. Tetrahedron Lett. 1991, 32, 4381. (b) Kitamura, M.; Tokunaga, M.; Ohkuma, T; Noyori, R. Tetrahedron Lett. 1991, 32, 4163. (c) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Org. Chem. 1992, 57, 4053. (d) Taber, D. F.; Silverberg, L. J. Tetrahedron Lett. 1991, 32, 4227. (e) King, S. A.; Thompson, A. S.; King, A. O.; Verhoeven, T. R. J. Org. Chem. 1992, 57, 6689. (f) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144. (g) Genet, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Cano De Andrade, M. C.; Laffitte, J. A. Tetrahedron 1994, 5, 665. (h) Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. (i) Burk, M. J.; Harper, T. G. P.; Kalberg, C. S. J. Am. Chem. Soc. 1995, 117, 4423.
16. For further studies of Ru-BINAP-mediated hydrogenation of β-keto esters, see: (a) Cesarotti, E.; Mauri, A.; Pallavicini, M.; Villa, L. Tetrahedron Lett. 1991, 32, 4381. (b) Kitamura, M.; Tokunaga, M.; Ohkuma, T; Noyori, R. Tetrahedron Lett. 1991, 32, 4163. (c) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Org. Chem. 1992, 57, 4053. (d) Taber, D. F.; Silverberg, L. J. Tetrahedron Lett. 1991, 32, 4227. (e) King, S. A.; Thompson, A. S.; King, A. O.; Verhoeven, T. R. J. Org. Chem. 1992, 57, 6689. (f) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144. (g) Genet, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Cano De Andrade, M. C.; Laffitte, J. A. Tetrahedron 1994, 5, 665. (h) Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. (i) Burk, M. J.; Harper, T. G. P.; Kalberg, C. S. J. Am. Chem. Soc. 1995, 117, 4423.
17. For further studies of Ru-BINAP-mediated hydrogenation of β-keto esters, see: (a) Cesarotti, E.; Mauri, A.; Pallavicini, M.; Villa, L. Tetrahedron Lett. 1991, 32, 4381. (b) Kitamura, M.; Tokunaga, M.; Ohkuma, T; Noyori, R. Tetrahedron Lett. 1991, 32, 4163. (c) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Org. Chem. 1992, 57, 4053. (d) Taber, D. F.; Silverberg, L. J. Tetrahedron Lett. 1991, 32, 4227. (e) King, S. A.; Thompson, A. S.; King, A. O.; Verhoeven, T. R. J. Org. Chem. 1992, 57, 6689. (f) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144. (g) Genet, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Cano De Andrade, M. C.; Laffitte, J. A. Tetrahedron 1994, 5, 665. (h) Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. (i) Burk, M. J.; Harper, T. G. P.; Kalberg, C. S. J. Am. Chem. Soc. 1995, 117, 4423.
18. For further studies of Ru-BINAP-mediated hydrogenation of β-keto esters, see: (a) Cesarotti, E.; Mauri, A.; Pallavicini, M.; Villa, L. Tetrahedron Lett. 1991, 32, 4381. (b) Kitamura, M.; Tokunaga, M.; Ohkuma, T; Noyori, R. Tetrahedron Lett. 1991, 32, 4163. (c) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Org. Chem. 1992, 57, 4053. (d) Taber, D. F.; Silverberg, L. J. Tetrahedron Lett. 1991, 32, 4227. (e) King, S. A.; Thompson, A. S.; King, A. O.; Verhoeven, T. R. J. Org. Chem. 1992, 57, 6689. (f) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144. (g) Genet, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Cano De Andrade, M. C.; Laffitte, J. A. Tetrahedron 1994, 5, 665. (h) Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. (i) Burk, M. J.; Harper, T. G. P.; Kalberg, C. S. J. Am. Chem. Soc. 1995, 117, 4423.
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