Enantioselective synthesis for the antipodes of slagenins B and C: establishment of absolute stereochemistry.
[reaction: see text] The total synthesis for the (-)-antipode of slagenin B (12) and the (+)-antipode of slagenin C (13) was achieved with the condensation of glyoxal hydrate 10 and urea as the key step. The absolute stereochemistries of naturally isolated slagenins B and C were assigned to be (9R,11R,15R)-1b and (9R,11S,15S)-1c, respectively.
Jiang
B
B
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P. R. China. jiangb@pub.sioc.ac.cn
Liu
J F
JF
Zhao
S Y
SY
D000818:Animals; D003603:Cytotoxins / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry*; D007093:Imidazoles / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism
D003603:Cytotoxins; D005663:Furans; D007093:Imidazoles; C416726:slagenin B; C416727:slagenin C