185300-90-7Relevant academic research and scientific papers
Enantioselective total synthesis and structure determination of the antiherpetic anthrapyran antibiotic AH-1763 IIa
Tietze, Lutz F.,Gericke, Kersten M.,Singidi, Ramakrishna Reddy
, p. 6990 - 6993 (2007/10/03)
(Chemical Equation Presented) The antiherpetic anthrapyran antibiotic (14S,16R)-AH-1763 IIa (see right-hand structure) and its (14R,16R) diastereomer have been prepared in enantioselective total syntheses. The relative and absolute stereochemistry of the
Highly diastereoselective synthesis of pederic acid derivatives
Roush, William R.,Marron, Thomas G.,Pfeifer, Lance A.
, p. 474 - 478 (2007/10/03)
A highly diastereoselective synthesis of methyl pederate (2) is described. A critical feature of the successful route is the introduction of the key C(7)-stereocenter at the stage of 4 via an enantioselective, syn-selective aldol reaction of aldehyde 5 and the chiral acyl oxazolidinone 6. Aldehyde 5, in turn, was prepared from the readily available aldol derivative 7 via a chelate-controlled reaction with allyltrimethylsilane. Intermediate 4 was elaborated to 2 via the intermediacy of 7-O-(3,4-dimethoxybenzyl)pederic acid (3), an intermediate in Kishi's syntheses of mycalamides A and B and onnamide A, by way of methyl pyranoside 16 and the fully protected pederic acid derivative 11.
