Diversity‐Oriented Synthesis of Amino Acid–Derived Scaffolds and Peptidomimetics: A Perspective

Design and synthesis of propellane derivatives and oxa-bowls via ring-rearrangement metathesis as a key step

“…Interestingly, the structurally complex propellane/oxa-bowl hybrids 7a , b were obtained through a four step synthetic sequence starting from simple DA adducts 3b , c , which are otherwise difficult to synthesize following conventional retrosynthetic routes. This methodology can easily be extended for diversity-oriented synthesis [ 37 ] by employing different dienes and dienophiles during the DA reaction sequence.…”

A diversity-oriented synthesis strategy enabling the combinatorial-type variation of macrocyclic peptidomimetic scaffolds

“… 14 Recent years have seen the development of several DOS-type strategies targeted at macrocyclic structures, 3 , 26 , 27 including macrocyclic peptidomimetics in particular. 28 Notable recent examples come from the research groups of Wessjohann, 28 , 29 Marcaurelle, 30 Marsault 9 and Harran. 31 Overall however, there still remains a relative lack of DOS strategies that are specifically directed towards macrocyclic peptidomimetics.…”

“…Reports beyond the proof-of-principle stage (that is, involving the application of such DOS strategies for the generation of large numbers of structurally diverse compounds based around a variety of macrocyclic peptidomimetic ring architectures) are rare. 9 , 18 , 28 …”

Enantioselective Synthesis of cis-Decalins Using Organocatalysis and Sulfonyl Nazarov Reagents

“…In order to extend these studies towards a diversity oriented synthesis [ 18 ], we envisaged the use of our methodology with β-keto-γ,δ-unsaturated sulfones under organocatalytic conditions to synthesize cis -decalins using cyclic unsaturated aldehydes as starting materials. Previously we have reacted cyclohexenecarboxaldehyde 6 with 1 in the presence of l -proline to obtain the corresponding 2 H -dihydropyran 7 [ 16 ] ( Scheme 2 ).…”