13C assignment of diastereotopic C-26 and -27 methyl groups of 24- methylenecholesterol: Steric course of hydrogen migration from C-24 to C-25 during its biosynthesis in higher plants

Chemical and Pharmaceutical Bulletin

Volumn 45, Issue 1, 1997, Pages 224-226

  Fujimoto, Yoshinori ^a   Ohyama, Kiyoshi ^a   Sato, Naoko ^a   Yamada, Junko ^b   Morisaki, Masuo ^b  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b KEIO UNIVERSITY   (Japan)

Author keywords

Catharanthus roseus; plant sterol; prochirality; stereochemistry; sterol biosynthesis; 24 sterol methyl transferase

Indexed keywords

24 METHYLENECHOLESTEROL; PHYTOSTEROL; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; MOLECULAR DYNAMICS; NONHUMAN; REACTION ANALYSIS; STEREOCHEMISTRY; STEROL SYNTHESIS;

EID: 0031012918     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.45.224     Document Type: Article

References (14)

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4. Arigoni D., Ciba Found. Symp., 60, 243-261 (1978).
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7. Nicotra F., Ronchetti F., Russo, G., Toma L., Magnetic Resonance Chem., 23, 134-136 (1985); the steric course in this paper was erroneously reported as Si-face migration based on the incorrect assignment of the diastereotopic methyl groups.
8. Nicotra F., Ronchetti F., Russo, G., Lugaro G., Casellato M., J. Chem. Soc., Perkin Trans. 1, 1981, 498-502.
9. Zhou W., Guo D., Nes W. D., Tetrahedron Lett., 1996, 1339-1342; references cited therein.
10. Guo D., Jia Z., Nes W. D., J. Am. Chem. Soc., 118, 8507-8508 (1996).
11. Fujimoto Y., Ikuina Y., Nagakari M., Kakinuma K., Ikekawa N., J. Chem. Soc., Perkin Trans. 1, 1991, 2041-2046.
12. The assignments eventually coincide with those reported in references 5, 6, and 10.
13. Ikuina Y., Kanzawa Y., Fujimoto Y., Kakinuma K., Chem. Pharm. Bull., 37, 1755-1758 (1989).
14. Yamada J., Morisaki M., Iwai K., Hamada H., Sato N., Fujimoto Y., Tetrahedron, in press.