Journal of natural products, 74(9), 1922-1930 (2011-09-09)
The synthesis of bis-steroidal pyrazines derived from 3-oxo-11,21-dihydroxypregna-4,17(20)-diene (4) and glycosylation of a D-ring side chain with α-L-rhamnose have been summarized. Rearrangement of steroidal pyrazine 10 to 14 was found to occur with boron triflouride etherate. Glycosylation of pyrazine 10
Chemistry and physics of lipids, 125(2), 93-101 (2003-09-23)
Methyl santalbate (methyl trans-11-octadecen-9-ynoate) from Sandal wood seed oil, Santalbum alum) was epoxidized to methyl trans-11,12-epoxy-octadec-9-ynoate (1). Treatment of compound 1 with tetrabutylammonium dihydrogentrifluoride, and boron trifluoride etherate gave the corresponding anti- (2a) (57%) and syn- (2b) (35%) fluorohydrin derivatives
Twenty-one 4α-acyloxy-2-chloropodophyllotoxin derivatives (5a-u), whose C-4 spatial configuration was mainly stereocontrolled by the configuration of C-2 chlorine atom, were unexpectedly prepared by the reaction of 2-chloropodophyllotoxin with carboxylic acids in the presence of BF(3)·Et(2)O. Compared with ordinary esterifications of carboxylic
Journal of the American Chemical Society, 131(2), 402-403 (2008-12-23)
C-H bond functionalization enables strategically new approaches to the synthesis of complex organic molecules including biologically active compounds, research probes and functional organic materials. To address the shortcomings of transition metal catalyzed processes, we have developed a new approach to
An easy and straightforward synthesis of 6,10b-diarylhexahydrobenzo[f]isoquinoline by the repeated treatment of boron trifluoride etherate (BF(3) x OEt(2)) is reported. The overall transformation from 4-arylpiperidin-3-one to benzo[f]isoquinoline proceeds via ring contraction, chain elongation, and intramolecular electrophilic cyclization in moderate yields.
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