Enantiocontrolled Synthesis and Absolute Configuration of (+)-Crooksidine, An Indole Alkaloid from Haplophyton Crooksii Using Chiral Piperideinol Block

Synlett

Volumn 1996, Issue 2, 1996, Pages 163-164

  Sakagami, Hideki ^a   Samizu, Kiyohiro ^a   Kamikubo, Takashi ^a   Ogasawara, Kunio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011911870     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5365     Document Type: Article

References (20)

1. Mroue, M. A.; Ghuman, M. A.; Alan, M. Phytochemistry 1993, 33, 217.
2. This natural product was also isolated from other plants: a) Crooks, P. A.; Robinson, G. F.; Smith, G. F. J. Chem. Soc., Chem. Commun. 1968, 1210. b) Robert, G. M. T.; Ahond, A.; Poupat, C.; Porter, P.; Jolles, C.; Jousselin, A.; Jacquemin, H. J. Nat. Prod. 1983, 46, 694. c) Atta-ur-Rahman; Zaman, K.; Perveen, S.; Habib-ur-Rehman; Muzaffar, A.; Choudhary, M. I.; Pervin, A. Phytochemistry 1991, 30, 1285.
3. This natural product was also isolated from other plants: a) Crooks, P. A.; Robinson, G. F.; Smith, G. F. J. Chem. Soc., Chem. Commun. 1968, 1210. b) Robert, G. M. T.; Ahond, A.; Poupat, C.; Porter, P.; Jolles, C.; Jousselin, A.; Jacquemin, H. J. Nat. Prod. 1983, 46, 694. c) Atta-ur-Rahman; Zaman, K.; Perveen, S.; Habib-ur-Rehman; Muzaffar, A.; Choudhary, M. I.; Pervin, A. Phytochemistry 1991, 30, 1285.
4. This natural product was also isolated from other plants: a) Crooks, P. A.; Robinson, G. F.; Smith, G. F. J. Chem. Soc., Chem. Commun. 1968, 1210. b) Robert, G. M. T.; Ahond, A.; Poupat, C.; Porter, P.; Jolles, C.; Jousselin, A.; Jacquemin, H. J. Nat. Prod. 1983, 46, 694. c) Atta-ur-Rahman; Zaman, K.; Perveen, S.; Habib-ur-Rehman; Muzaffar, A.; Choudhary, M. I.; Pervin, A. Phytochemistry 1991, 30, 1285.
5. Palmisano, G.; Santagostino, M.; Riva, S.; Sisti, M. Tetrahedron: Asymmetry 1995, 6, 1229.
6. A pertinent monograph, see: Wong, C. -H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994.
7. Imanishi, T.; Shin, H.; Hanaoka, M.; Momose, T.; Imanishi, I. Chem. Pharm. Bull. 1982, 30, 3617.
8. Mitsunobu, O. Synthesis 1981, 1; Hughes, D. L. Org. Reactions 1992, 42, 335.
9. Mitsunobu, O. Synthesis 1981, 1; Hughes, D. L. Org. Reactions 1992, 42, 335.
10. Johnson, W. S.; Werthemann, L.; Bartlett, W. R.; Brocksom, T.; Li, T.; Faulkner, D. J.; Petersen, M. R. J. Am. Chem. Soc. 1970, 92, 741.
11. Nakagawa, I.; Hata, T. Tetrahedron Lett. 1975, 1409; Nakagawa, I.; Aki, K.; Hata, T. J. Chem. Soc., Perkin Trans I 1983, 1315.
12. Nakagawa, I.; Hata, T. Tetrahedron Lett. 1975, 1409; Nakagawa, I.; Aki, K.; Hata, T. J. Chem. Soc., Perkin Trans I 1983, 1315.
13. Plieninger, H.; Müller, W.; Weiwerth, K. Chem. Ber. 1964, 97, 667.
14. In some cases, a minor amount (∼4%) of (+)-(R)-decarbomethoxy-15,20:16,17-tetrahydrosecodine (2) was also generated.
15. Srikrishna, A.; Sattigeri, J. A.; Viswajanani, R.; Yelamaggad, C. V. Synlett 1995, 93.
16. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 43, 4156; J. Am. Chem. Soc. 1991, 113, 7277.
17. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 43, 4156; J. Am. Chem. Soc. 1991, 113, 7277.
18. 3) (>99% ee by hplc using a chiral column: CHIRALCEL OJ, 2% i-PrOH-hexane), to that of the enantiomer.
19. Lipase-mediated transesterification of the racemic alcohol [(±)-3] - A mixture of (±)-3 (1.68 g, 7.21 mmol) and vinyl acetate (3.3 mL, 35.8 mmol) in dichloromethane (80 mL) was stirred with lipase PS on Celite (1.62 g) at 40 °C for 29 h. After filtration through a Celite pad, the mixture was evaporated under reduced pressure. The residue was chromatographed on silica gel (150 g) to give the acetate [(-)-4] (921 mg, 46.5%, >99% ee) from AcOEt/hexane (1:3) fraction and the alcohol [(+)-3] (800 mg, 47.6%, >99% ee) from AcOEt/hexane (1:1) fraction.
20. 2 284.2253, found 284.2234.