87896-52-4Relevant academic research and scientific papers
Applications of vinylogous Mannich reactions. Total synthesis of the angiotensin converting enzyme inhibitor (-)-A58365A
Reichelt, Andreas,Bur, Scott K,Martin, Stephen F
, p. 6323 - 6328 (2007/10/03)
A concise enantiospecific synthesis of the angiotensin converting enzyme inhibitor (-)-A58365A (7) has been achieved following a strategy in which a vinylogous Mannich reaction and a lactone-lactam rearrangement served as the key transformations. The trimethylsilyloxyfuran derived from 25, which was prepared from the known sulfoxide 16, served as the nucleophilic partner in a vinylogous Mannich reaction with the chiral N-acyliminium ion that was generated in situ from the aminal 26. Addition of a further quantity of TMSOTf cleaved the N-Boc group from the adducts 27 to give a mixture of diastereomeric amino butenolides 28. Treatment of this mixture with LiOMe/MeOH furnished 10, and acid-catalyzed hydrolysis of the methyl ester groups delivered (-)-A58365A in 37% overall yield over the longest linear sequence of eight steps.
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 via an isomuenchnone cycloaddition reaction.
Straub,Padwa
, p. 83 - 85 (2008/02/11)
[formula: see text] The angiotensin converting enzyme inhibitor (-)-A58365A (1) was synthesized by a process based on the [3 + 2]-cycloaddition reaction of a phenylsulfonyl-substituted isomuenchnone intermediate. The starting material for this process was prepared from L-pyroglutamic acid and involved using a diazo-phenylsulfonyl-substituted pyrrolidine imide. Treatment of the diazoimide with Rh2(OAc)4 in the presence of methyl vinyl ketone afforded a 3-hydroxy-2-pyridone derivative which was subsequently converted to the ACE inhibitor in six additional steps.
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
