Stereoselective Total Synthesis of Pyrrolizidine Alkaloid Bases: (-)-Rosmarinecine and (-)-Isoretronecanol

Journal of the American Chemical Society

Volumn 105, Issue 12, 1983, Pages 4096-4097

  Tatsuta, Kuniaki ^a   Takahashi, Hideaki ^a   Amemiya, Yoshiya ^a   Kinoshita, Mitsuhiro ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0004982288     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00350a061     Document Type: Letter

References (25)

1. For examples, see: Bull, L. B.; Culvenor C. C. J.; Dick, A. T. “The Pyrrolizidine Alkaloids” North-Holland: Amsterdam, 1968.
2. Wood, H. C. S.; Wrigglesworth, R. “Rodd's Chemistry of Carbon Compounds” Coffey S., Ed.; Elsevier: Amsterdam, 1977; Vol. IVB, pp 7–62.
3. Robins, D. J. Adv. Heterocycl. Chem. 1979, 24, 247–291.
4. Three syntheses affording optically active (-)-isoretronecanol have been reported [(a) Rüeger, H.; Benn, M. Heterocycles 1982, 19, 1677–1680.
5. Robins D. J.; Sakdarat, S. J. Chem. Soc, Perkin Trans. 1, 1981, 909–913.
6. Robins D. J.; Sakdarat S. J. Chem. Soc, Chem. Commun. 1979, 1181–1182.
7. Takano S.; Ogawa N.; Ogasawara, K. Heterocycles 1981, 16, 915–916] with >90%, 90%, and 33% optical purity, respectively.
8. A synthon for some necines has been synthesized with 99% optical purity: Rüeger, H.; Benn, M. Heterocycles 1982, 19, 23–25.
9. Richardson M. F.; Warren F. L. J. Chem. Soc. 1943, 452–454.
10. Porter L. A.; Geissman T. A. J. Org. Chem. 1962, 27, 4132–4134.
11. The natural alkaloid rosmarinine, from which (-)-rosmarinecine (1) could be obtained by alkaline hydrolysis, was provided by Prof. S. E. Drewes, University of Natal, S. Africa; see ref 3a.
12. Adams R.; Hamlin K. E. Jr., J. Am. Chem. Soc. 1942, 64, 2597–2599.
13. Recent synthesis of the racemate: Iwashita, T.; Kusumi T.; Kakisawa H. J. Org. Chem. 1982, 47, 230–233 and references therein.
14. Tatsuta K.; Miyashita S.; Akimoto K.; Kinoshita M. Bull. Chem. Soc. Jpn. 1982, 55, 3254–3256.
15. Purchased from Aldrich Chemical Co. See also: (a) Nagasawa, T.; Kuroiwa K.; Narita K.; Isowa Y. Bull. Chem. Soc. Jpn. 1973, 46, 1269–1272.
16. Ikeda D.; Miyasaka T.; Yoshida M.; Horiuchi Y.; Kondo S.; Umezawa, H. J. Antibiot. 1979, 32, 1365–1366.
17. Still, W. C.; McDonald J. H. III, Tetrahedron Lett. 1980, 21, 1031–1034.
18. Evans D. A.; Nelson J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1–115.
19. Tsuda Y.; Nunozawa T.; Yoshimoto, K. Chem. Pharm. Bull. 1980, 28, 3223–3231.
20. Kinoshita M.; Ohsawa N.; Gomi, S. Carbohydr. Res. 1982, 109, 5–23.
21. ApSimon J. W.; Chau A. S. Y.; Craig W. G.; Krehm H. Can. J. Chem. 1967, 45, 1439–1445.
22. Ohfune Y.; Tomita M. J. Am. Chem. Soc. 1982, 104, 3511–3513.
23. The 1H NMR of the natural product was provided by Prof. L. W. Smith, CSIRO, Australia.
24. Aasen A. J.; Culvenor C.C.J. J. Org. Chem. 1969, 34, 4143–4147.
25. Authentic samples of the natural and racemic products were provided by Prof. L. W. Smith, CSIRO, Australia and Prof. H. Kakisawa, The University of Tsukuba, respectively, and the 1H NMR spectra were also provided by them and Prof. H. W. Pinnick, The University of Georgia.