Highly stereoselective construction of 4,6-cis-substituted quinolizidine ring core: An application to enantioselective total synthesis of the marine alkaloid clavepictines A, B and pictamine

Tetrahedron

Volumn 55, Issue 52, 1999, Pages 15209-15224

  Toyooka, Naoki ^a   Yotsui, Yasuhito ^a   Yoshida, Yasuko ^a   Momose, Takefumi ^a   Nemoto, Hideo ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; NATURAL PRODUCT; QUINOLIZIDINE DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG CONFORMATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033601457     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00996-5     Document Type: Article

References (16)

1. Raub, M. F.; Cardellina, II, J. H.; Choudhary, M. I.; Ni, C.-Z.; Clardy, J.; Alley, M. C. J. Am. Chem. Soc. 1991, 113, 3178-3180.
2. Kong, F.; Faulkner, D. J. Tetrahedron Lett. 1991, 32, 3667-3668.
3. Toyooka, N.; Yoshida, Y.; Momose, T. Tetrahedron Lett. 1995, 36, 3715-3718; Toyooka, N.; Yoshida, Y.; Yotsui, Y.; Momose, T. J. Org. Chem. 1999, 64, 4914-4919.
4. Toyooka, N.; Yoshida, Y.; Momose, T. Tetrahedron Lett. 1995, 36, 3715-3718; Toyooka, N.; Yoshida, Y.; Yotsui, Y.; Momose, T. J. Org. Chem. 1999, 64, 4914-4919.
5. The intramolecular conjugate addition reaction with nitrogen nucleophiles has been recognized as a powerful tool for construction of piperidine ring system, see: Akiyama, E.; Hirama, M. Synlett 1996, 100-102 and references cited therein.
6. For preliminary accounts, see: Toyooka, N.; Yotsui, Y.; Yoshida, Y.; Momose, T. J. Org. Chem. 1996, 61, 4882-4883; Another enantioselective total synthesis of clavepictines A and B; see: Ha, J. D.; Lee, D.; Cha, J. K. J. Org. Chem. 1997, 62, 4550-4551.
7. For preliminary accounts, see: Toyooka, N.; Yotsui, Y.; Yoshida, Y.; Momose, T. J. Org. Chem. 1996, 61, 4882-4883; Another enantioselective total synthesis of clavepictines A and B; see: Ha, J. D.; Lee, D.; Cha, J. K. J. Org. Chem. 1997, 62, 4550-4551.
8. Hart, D. J.; Leroy, V. Tetrahedron 1995, 51, 5757-5770.
9. 3 as follows: (equation presented)
10. 6 position and the bridge-head are axial orientation. This observation means that the relative stereochemistry of methyl and methoxycarbonylmethyl groups is trans relationship, and the ring juncture is also trans relationship.
11. Hoffmann, R. W. Chem. Rev. 1989, 89, 1841-1873.
12. Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon: New York, 1983; pp 209-290.
13. The vinylogous urethane 5 was prepared from (v) obtained above as follows: (equation presented)
14. The piperidine 7 was prepared from (iv) obtained above as follows: (equation presented)
15. Dong, Q.; Anderson, C. E.; Ciufolini, M. A. Tetrahedron Lett. 1995, 36, 5681-5682.
16. w = 6.4 %.