115592-74-0Relevant academic research and scientific papers
Synthesis of the aromatic unit of calicheamicin γ1 I
Hu, Yong-Zhou,Clive, Derrick L. J.
, p. 1421 - 1424 (2007/10/03)
Vanillin and piperonal are each converted into methyl 2,3-dimethoxy-6-methyl-4-(prop-2-enyl)benzoate 12, and this is then elaborated into methyl 4-hydroxy-3-iodo-5,6-dimethoxy-2-methylbenzoate 24, which represents the aromatic unit of calicheamicin γ1I.
Total synthesis of calicheamicin γ1I. 1. Synthesis of the oligosaccharide fragment
Groneberg,Miyazaki,Stylianides,Schulze,Stahl,Schreiner,Suzuki,Iwabuchi,Smith,Nicolaou
, p. 7593 - 7611 (2007/10/02)
The first total synthesis of the calicheamicin γ1I oligosaccharide fragment in the form of its methyl glycoside (62) has been achieved. The synthetic challenge of the B-ring was recognized and studied initially, resulting in a novel and unique solution to the stereochemical problems posed involving a [3,3]-sigmatropic rearrangement of an allylic thionoimidazolide (111). This chemistry was initially worked out on a model for the ABC-ring system (47) and then successfully applied to the real system. The success of this synthesis has enabled the completion of the first synthesis of the natural product itself, calicheamicin γ1I (1), as will be described in the following papers in this issue.
SYNTHESES OF 4-HYDROXY-5-IODO-2,3-DIMETHOXY-6-METHYLBENZOIC ACID AND 5-BROMO-4-HYDROXY-2,3-DIMETHOXY-6-METHYLBENZOIC ACID - AROMATIC CONSTITUENTS OF THE CALICHEMICINS
Laak, Kai van,Scharf, Hans-Dieter
, p. 5511 - 5516 (2007/10/02)
4-Hydroxy-5-iodo-2,3-dimethoxy-6-methylbenzoic acid (1) and 5-bromo-4-hydroxy-2,3-dimethoxy-6-methylbenzoic acid (2) are the polysubstituted aromatic carboxylic acids found in calichemicin antibiotics.The title compounds are synthesized on preparative sca
