206867-88-1Relevant articles and documents
Synthesis of the angiotensin-converting enzyme inhibitor (±)-A58365A
Clive, Derrick L. J.,Coltart, Don M.
, p. 2519 - 2522 (1998)
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
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).
Cross-metathesis of unsaturated α-amino acid derivatives
Biagini, Stefano C. G.,Gibson, Susan E.,Keen, Stephen P.
, p. 2485 - 2499 (2007/10/03)
Cross-metathesis of homoallylglycine derivatives with aryl- and alkyl-substituted alkenes using the ruthenium catalyst (Cy3P)2Cl2Ru=CHPh 1 has been achieved in 43-55 and 55-66% yield respectively. Allylglycine, vinylglycine and dehydroalanine derivatives have also been examined. Whilst cross-metathesis of allylglycine derivatives with alkyl-substituted alkenes using catalyst 1 may be regarded as a synthetically useful procedure, cross-metathesis reactions of vinylglycine and dehydroalanine derivatives using catalyst 1 are non-viable. Attachment of FmocHagOH 13 to a capped Wang resin, cross-metathesis with dodec-1-ene, and product removal from the resin gives the cross-metathesis product in 74% yield based on FmocHagOH.
