Convergent de novo synthesis of vineomycinone B2 methyl ester
An efficient de novo synthesis of vineomycinone B2 methyl ester has been achieved. The longest linear route required only 14 steps from achiral commercially available starting materials (4.0% overall yield). The key transformations included the de novo asymmetric synthesis of two key fragments, which were joined by a convergent late stage Suzuki's glycosylation for the construction of the aryl β-C-glycoside. A subsequent BBr3 one-pot debenzylation, demethylation and air oxidation provided vineomycinone B2 methyl ester.
Chen, Qian,Zhong, Yashan,O'Doherty, George A.
supporting information
p. 6806 - 6808
(2013/07/26)
Indium-Mediated Allylation of Aldehydes: A Convenient Route to 2-Deoxy and 2,6-Dideoxy Carbohydrates
The allylation of protected polyhydroxy aldehydes 1 and 14 has been achieved by indium metal with ultrasound promotion generating the diastereomeric pair of homoallylic polyols 3, 4 and 16, 17 respectively with moderate to good stereoselectivity.Pursuing this allylation strategy with the corresponding deprotected polyhydroxy aldehydes led to the same pair of homoallylic polyols but with a quite different ratio of the diastereomers generated.The polyols were further transformed to 2-deoxy (5 and 6) and 2,6-dideoxy (18 and 19) carbohydrates by ozonolysis.
Binder, Wolfgang H.,Prenner, Reinhard H.,Schmid, Walther
p. 749 - 758
(2007/10/02)
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