Enantioselective total syntheses of slagenins A-C and their antipodes.
Full details of the total syntheses of slagenins A-C (1a-c) and their antipodes (2a-c), novel bromopyrrole alkaloids with a unique tetrahydrofuro[2,3-d]imidazolidin-2-one moiety, are described in which their absolute stereochemistry was established. The key step in the syntheses involves the efficient condensation of dihydrofuran-3-one or glyoxal with urea to construct the slagenin bicycle core.
Jiang
Biao
B
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, PR China. jiangb@pub.sioc.ac.cn
Liu
Jia-Feng
JF
Zhao
Sheng-Yin
SY
D000470:Alkaloids / Q000138:chemical synthesis*; D000818:Animals; D020650:Combinatorial Chemistry Techniques; D005663:Furans / Q000138:chemical synthesis*; D007093:Imidazoles / Q000138:chemical synthesis*; D007564:Japan; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D005663:Furans; D007093:Imidazoles; C416728:slagenin A; C416726:slagenin B; C416727:slagenin C