222739-35-7Relevant academic research and scientific papers
Synthesis of the angiotensin-converting enzyme inhibitors (-)-A58365A and (-)-A58365B from a common intermediate
Clive, Derrick L. J.,Coltart, Don M.,Zhou, Yuanxi
, p. 1447 - 1454 (2007/10/03)
(-)-A58365A (1) and (-)-A58365B (2), which are inhibitors of angiotensin-converting enzyme, were synthesized from the subunits 9 and 10. These were coupled, and the resulting individual amides 17a,b were converted by ozonolysis into aldehydes 18a,b, which underwent cyclodehydration to the enamides 19a,b. Treatment with a stannane served to generate the vinyl stannanes 20a,b, from which ketones 22a,b were produced by protodestannylation and ozonolysis. Base treatment and hydrogenolysis then afforded (-)-A58365A (1). The intermediates 17a,b were also converted into aldehydes 26a,b by hydroboration and oxidation, and a similar sequence to that used for (-)-A58365A was then applied in order to complete the first enantiospecific synthesis of the congener, (-)-A58365B (2).
Synthesis of the angiotensin-converting enzyme inhibitor (±)-A58365A
Clive, Derrick L. J.,Coltart, Don M.
, p. 2519 - 2522 (2007/10/03)
Crystalline (±)-A58365A (1), an inhibitor of angiotensin-converting enzyme, was synthesized by a process based on enyne radical cyclization (13a,b → 14a,b). The starting material for this process was constructed by coupling the spiro lactone 6 with the am
