Catalytic asymmetric synthesis of either enantiomer of the calabar alkaloids physostigmine and physovenine

Journal of the American Chemical Society

Volumn 120, Issue 26, 1998, Pages 6500-6503

  Matsuura, Takaharu ^a,b   Overman, Larry E ^a   Poon, Daniel J ^a,c  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b SHIONOGI AND CO LTD   (Japan)

^c Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; PHYSOSTIGMINE; PHYSOVENINE;

ARTICLE; CATALYSIS; CYCLIZATION; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0032496928     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja980788+     Document Type: Article

References (37)

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19. For asymmetric total syntheses published since Takano's review, see refs 9, 15, 18 and the following: (a) Takano, S.; Moriya, M.; Iwabuchi, Y.; Ogasawara K. Chem. Lett. 1990, 109. (b) Takano, S.; Sato, T.; Inomata, K.; Ogasawara, K. Heterocycles 1990, 31, 411. (c) Takano, S.; Moriya, M.; Ogasawara K. J. Org. Chem. 1991, 56, 5982. (d) Node, M.; Itoh, A.; Masaki, Y.; Fuji, K. Heterocycles 1991, 32, 1705. (e) Marino, J. P.; Bogdan, S.; Kimura, K. J. Am. Chem. Soc. 1992, 114, 5566. (f) Node, M.; Hao, X., Nishide, K.; Fuji, K. Chem. Pharm. Bull. 1996, 44, 715.
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31. A Diacel Chiralcel OD column (9:1 hexane-i-PrOH) provided baseline resolution of enantiomers; chromatograms are provided in the Supporting Information.
32. Yu, Q.-S.; Brossi, A. Heterocycles 1988, 27, 745.
33. 25
34. Since 25% of the steps are involved in preparing (Z)-siloxybutenoic acid 12, we investigated Heck cyclizations of anilides prepared from commercially available methacrylic acid. Although carbonylative Heck cyclizations could be realized (eq 1), enantioselection was never satisfactory. Results of these investigations are briefly summarized in the Supporting Information. Equation presented
35. 19 Conventional silica gel flash chromatography is abbreviated as sgc.
36. The enantiomeric excess was determined by HPLC analysis on a Diacel Chiralcel OD column using as eluent: (a) 99:1 hexane-i-PrOH; (b) 99.5:0.5 hexane-i-PrOH.
37. The enatiomeric excess was determined by HPLC analysis on a Diacel Chiralcel OJ column (85:15 hexane-i-PrOH).