Asymmetric Total Syntheses of (+)-Coronafacic Acid and (+)-Coronatine

Bioscience, Biotechnology and Biochemistry

Volumn 61, Issue 4, 1997, Pages 752-753

  Toshima, Hiroaki ^a   Nara, Shinji ^a   Ichihara, Akitami ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

1, 6 conjugate addition; Asymmetric synthesis; Coronafacic acid; Coronamic acid; Coronatine

Indexed keywords

EID: 0030808373     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.61.752     Document Type: Article

References (17)

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13. Satisfactory spectroscopic data were obtained for all the new compounds.
14. H. Grebe, A. Lange, H. Riechers, K. Kieslich, W. Viergutz, P. Washausen, and E. Winterfelt, J. Chem. Soc., Perkin Trans. 1, 1991, 2651-2655.
15. Column, Chiralcel OC® (ø 4.6 × 250 mm); eluent, hexane/2-propanol (96/4); flow rate, 0.3ml/min; detection, UV 220 nm; retention times: 8, 36 min; enantiomer of 8, 40 min.
16. The same column and conditions as those in ref. 8 were used; detection by UY at 240 nm retention times: 10a, 64 min; 10b, 59 min. Although the first reported mp of natural (+)-2 is described as 125-126°C in ref. 1 a, the corrected mp value is described as 141 -142°C in the thesis of Dr. K. Shiraishi (Hokkaido University, 1978). Furthermore, Prof. M. Nakayama has reported mp 142-143°C for his synthetic (+)-2 ([oi]j3° + 109°) and our natural sample in ref. 3a. H. Toshima and A. Ichihara, Biosci. Biotech. Biochem., 59, 495-500 (1995).
17. Although the mp of natural (+)-l is described as 151-153°C in ref. la, 161-163°C is the corrected value in the thesis of Dr. K. Shiraishi. Since we have no natural sample at the present time, the specific rotations, which may be influenced by the temperature, cannot be compared directly.