Synthesis of the quinolizidine alkaloids (-)-lasubine II and (±)-myrtine by conjugate addition and intramolecular acylation of amino esters with acetylenic sulfones

Journal of Organic Chemistry

Volumn 70, Issue 3, 2005, Pages 967-972

  Back, Thomas G ^a   Hamilton, Michael D ^a   Lim, Vania J J ^a   Parvez, Masood ^a  

^a UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACYLATION; ADDITION REACTIONS; ESTERS; REACTION KINETICS; REDUCTION; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

DESULFONYLATION; QUINOLIZIDINE ALKALOIDS; STEREOSELECTIVE REDUCTION; SULFONES;

AMINES;

1 (4 TOLUENESULFONYL)PROPYNE; 3 CHLORO 4 METHYL 3 (4 TOLUENESULFONYL)3,4 DEHYDROQUINOLIZIDIN 2 ONE; 4 METHYL 3 (4 TOLUENESULFONYL)3,4 DEHYDROQUINOLIZIDIN 2 ONE; ACETIC ACID DERIVATIVE; ACETYLENIC SULFONE; ALKALOID; ESTER DERIVATIVE; METHYL 2 PIPERIDYL ACETATE; QUINOLIZIDINE DERIVATIVE; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ADDITION REACTION; ARTICLE; CHEMICAL STRUCTURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 13244287868     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048284j     Document Type: Article

References (75)

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27. For syntheses of (±)-lasubine II, see: (f) Bardot, V.; Gardette, D.; Gelas-Mialhe, Y.; Gramain, J.-C.; Remuson, R. Heterocycles 1998, 48, 507. (g) Pilli, R. A.; Dias, L. C.; Maldaner, A. O. J. Org. Chem. 1995, 60, 717. (h) Pilli, R. A.; Dias, L. C.; Maldaner, A. O. Tetrahedron Lett. 1993, 34, 2729. (i) Brown, J. D.; Foley, M. A.; Comins, D. L. J. Am. Chem. Soc. 1988, 110, 7445. (j) Narasaka, K.; Ukaji, Y.; Yamazaki, S. Bull. Chem. Soc. Jpn. 1986, 59, 525. (k) Hoffmann, R. W.; Endesfelder, A. Liebigs Ann. Chem. 1986, 1823. (l) Iida, H.; Tanaka, M.; Kibayashi, C. J. Org. Chem. 1984, 49, 1909. (m) Takano, S.; Shishido, K. Chem. Pharm. Bull. 1984, 32, 3892. (n) Quick, J.; Ramachandra, R. Tetrahedron 1980, 36, 1301.
28. For syntheses of (±)-lasubine II, see: (f) Bardot, V.; Gardette, D.; Gelas-Mialhe, Y.; Gramain, J.-C.; Remuson, R. Heterocycles 1998, 48, 507. (g) Pilli, R. A.; Dias, L. C.; Maldaner, A. O. J. Org. Chem. 1995, 60, 717. (h) Pilli, R. A.; Dias, L. C.; Maldaner, A. O. Tetrahedron Lett. 1993, 34, 2729. (i) Brown, J. D.; Foley, M. A.; Comins, D. L. J. Am. Chem. Soc. 1988, 110, 7445. (j) Narasaka, K.; Ukaji, Y.; Yamazaki, S. Bull. Chem. Soc. Jpn. 1986, 59, 525. (k) Hoffmann, R. W.; Endesfelder, A. Liebigs Ann. Chem. 1986, 1823. (l) Iida, H.; Tanaka, M.; Kibayashi, C. J. Org. Chem. 1984, 49, 1909. (m) Takano, S.; Shishido, K. Chem. Pharm. Bull. 1984, 32, 3892. (n) Quick, J.; Ramachandra, R. Tetrahedron 1980, 36, 1301.
29. For syntheses of (±)-lasubine II, see: (f) Bardot, V.; Gardette, D.; Gelas-Mialhe, Y.; Gramain, J.-C.; Remuson, R. Heterocycles 1998, 48, 507. (g) Pilli, R. A.; Dias, L. C.; Maldaner, A. O. J. Org. Chem. 1995, 60, 717. (h) Pilli, R. A.; Dias, L. C.; Maldaner, A. O. Tetrahedron Lett. 1993, 34, 2729. (i) Brown, J. D.; Foley, M. A.; Comins, D. L. J. Am. Chem. Soc. 1988, 110, 7445. (j) Narasaka, K.; Ukaji, Y.; Yamazaki, S. Bull. Chem. Soc. Jpn. 1986, 59, 525. (k) Hoffmann, R. W.; Endesfelder, A. Liebigs Ann. Chem. 1986, 1823. (l) Iida, H.; Tanaka, M.; Kibayashi, C. J. Org. Chem. 1984, 49, 1909. (m) Takano, S.; Shishido, K. Chem. Pharm. Bull. 1984, 32, 3892. (n) Quick, J.; Ramachandra, R. Tetrahedron 1980, 36, 1301.
30. For syntheses of (±)-lasubine II, see: (f) Bardot, V.; Gardette, D.; Gelas-Mialhe, Y.; Gramain, J.-C.; Remuson, R. Heterocycles 1998, 48, 507. (g) Pilli, R. A.; Dias, L. C.; Maldaner, A. O. J. Org. Chem. 1995, 60, 717. (h) Pilli, R. A.; Dias, L. C.; Maldaner, A. O. Tetrahedron Lett. 1993, 34, 2729. (i) Brown, J. D.; Foley, M. A.; Comins, D. L. J. Am. Chem. Soc. 1988, 110, 7445. (j) Narasaka, K.; Ukaji, Y.; Yamazaki, S. Bull. Chem. Soc. Jpn. 1986, 59, 525. (k) Hoffmann, R. W.; Endesfelder, A. Liebigs Ann. Chem. 1986, 1823. (l) Iida, H.; Tanaka, M.; Kibayashi, C. J. Org. Chem. 1984, 49, 1909. (m) Takano, S.; Shishido, K. Chem. Pharm. Bull. 1984, 32, 3892. (n) Quick, J.; Ramachandra, R. Tetrahedron 1980, 36, 1301.
31. For syntheses of (±)-lasubine II, see: (f) Bardot, V.; Gardette, D.; Gelas-Mialhe, Y.; Gramain, J.-C.; Remuson, R. Heterocycles 1998, 48, 507. (g) Pilli, R. A.; Dias, L. C.; Maldaner, A. O. J. Org. Chem. 1995, 60, 717. (h) Pilli, R. A.; Dias, L. C.; Maldaner, A. O. Tetrahedron Lett. 1993, 34, 2729. (i) Brown, J. D.; Foley, M. A.; Comins, D. L. J. Am. Chem. Soc. 1988, 110, 7445. (j) Narasaka, K.; Ukaji, Y.; Yamazaki, S. Bull. Chem. Soc. Jpn. 1986, 59, 525. (k) Hoffmann, R. W.; Endesfelder, A. Liebigs Ann. Chem. 1986, 1823. (l) Iida, H.; Tanaka, M.; Kibayashi, C. J. Org. Chem. 1984, 49, 1909. (m) Takano, S.; Shishido, K. Chem. Pharm. Bull. 1984, 32, 3892. (n) Quick, J.; Ramachandra, R. Tetrahedron 1980, 36, 1301.
32. For syntheses of (±)-lasubine II, see: (f) Bardot, V.; Gardette, D.; Gelas-Mialhe, Y.; Gramain, J.-C.; Remuson, R. Heterocycles 1998, 48, 507. (g) Pilli, R. A.; Dias, L. C.; Maldaner, A. O. J. Org. Chem. 1995, 60, 717. (h) Pilli, R. A.; Dias, L. C.; Maldaner, A. O. Tetrahedron Lett. 1993, 34, 2729. (i) Brown, J. D.; Foley, M. A.; Comins, D. L. J. Am. Chem. Soc. 1988, 110, 7445. (j) Narasaka, K.; Ukaji, Y.; Yamazaki, S. Bull. Chem. Soc. Jpn. 1986, 59, 525. (k) Hoffmann, R. W.; Endesfelder, A. Liebigs Ann. Chem. 1986, 1823. (l) Iida, H.; Tanaka, M.; Kibayashi, C. J. Org. Chem. 1984, 49, 1909. (m) Takano, S.; Shishido, K. Chem. Pharm. Bull. 1984, 32, 3892. (n) Quick, J.; Ramachandra, R. Tetrahedron 1980, 36, 1301.
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