87896-53-5Relevant academic research and scientific papers
Synthesis of crystalline (±)-A58365B - An inhibitor of angiotensin-converting enzyme
Clive, Derrick L. J.,Zhou, Yuanxi,De Lima, Denis Pires
, p. 1463 - 1464 (1996)
A58365B 1, an inhibitor of angiotensin-converting enzyme, is synthesized from two subunits, spiro lactone 5 and ε-hydroxynorleucine methyl ester 6, by a process based on enyne radical cyclization (9a,b → 11a,b).
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).
Anodic amide oxidations: Total syntheses of (-)-A58365A and (±)-A583665B
Wong, Poh Lee,Moeller, Kevin D.
, p. 11434 - 11445 (2007/10/02)
An anodic amide oxidation-iminium ion cyclization strategy for annulating rings into amines and amino acid derivatives has been used to synthesize the angiotensin-convertmg enzyme inhibitors (-)-A58365A and (± A58365B. Both svntheses take advantage of the
