Regioselective oxyfunctionalization of brassinosteroids by methyl(trifluoromethyl)dioxirane: Synthesis of 25-hydroxy-brassinolide and 25-hydroxy-24-epibrassinolide by direct C-H insertion

Tetrahedron

Volumn 52, Issue 32, 1996, Pages 10653-10658

  Voigt, Brunhilde ^a   Porzel, Andrea ^a   Golsch, Dieter ^b   Adam, Waldemar ^b   Adam, Günter ^a  

^a LEIBNIZ INSTITUTE OF PLANT BIOCHEMISTRY   (Germany)

^b UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BRASSINOLIDE; PHYTOHORMONE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030570907     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00587-X     Document Type: Article

References (13)

1. 1. For reviews, see: (a) Marquardt, V.; Adam, G., Recent Advances in Brassinosteroid Research. In: Ebing, W. (Ed.) Chemistry of Plant Protection, 1991, Springer, Berlin, Vol. 7; 103-139.
2. (b) Sakurai, A.; Fujioka, S. Plant Growth Regul. 1993, 13, 147-159.
3. (c) Adam, G.; Porzel, A.; Schmidt, J.; Schneider, B.; Voigt, B., New Developments in Brassinosteroid Research. In: Atta-ur-Rahman (Ed) Studies in Natural Products Chemistry; Elsevier: Amsterdam, London, New York, Tokyo, Vol. 18, 495-549.
4. 2. Hai, T.; Schneider, B.; Adam, G., Phytochemistry 1995, 40, 443-448.
5. 3. Hai, T.; Schneider, B.; Porzel, A.; Adam, G., Phytochemistry 1996, 41, 197-201.
6. 4. Cutler, H. G., Advances in the Use of Brassinosteroids. In: ACS Symposium Series 551, American Chemical Society, Washington DC 1994, 85-102.
7. 5. For recent review, see: Adam, W.; Curci, R., Hadjiarapoglou, L.; Mello, R.: Dioxiranes, Threemembered Ring Cyclic Peroxides. In Organic Peroxides; Ando, W. Ed.; John Wiley and Sons, Inc.: New York 1992; 4, 195-219.
8. 6. Bovicelli, P.; Lupattelli, P.; Mincione, E.; Prencipe, T.; Curci, R., J. Org. Chem. 1992, 57, 2182-2184 and 5052-5054.
9. 7. Voigt, B.; Porzel, A.; Golsch, D.; Adam, W.; Adam, G., unpublished results.
10. 8. In the case of the corresponding 2α,3α,22,23-diisopropylidenedioxy derivatives the acetonide function at ringA was involved into the reaction leading to a mixture of regioisomeric ketols, see, ref. 7.
11. 9. An analogous ratio of two regioisomers was found also in the synthesis of 2-deoxy-24-epibrassinolide, see, Voigt, B.; Schmidt, J.; Adam, G., Tetrahedron 1996, 52, 1997-2004.
12. 10. Arima, M.; Yokota, T.; Takahashi, N., Phytochemistry 1984, 23, 1587-1591.
13. 11. Voigt, B.; Takatsuto, S.; Yokota, T.; Adam, G., J. Chem. Soc. Perkin Trans 1 1995, 1495-1498.