ABSTRACT
A simple and practical one-pot, two-directional approach to access olefinic esters through simultaneous breaking and making of olefins using ozonolysis of alkenyl aryl selenides is disclosed. The scope of the method with a variety of examples is demonstrated, and the end products obtained here are useful building blocks. As a direct application of the present method, the macrocyclic core of potent anti-inflammatory natural cyclic peptides, solomonamides, is synthesized.
Subject(s)
Alkenes/chemistry , Anti-Inflammatory Agents, Non-Steroidal/chemical synthesis , Peptides, Cyclic/chemical synthesis , Anti-Inflammatory Agents, Non-Steroidal/chemistry , Anti-Inflammatory Agents, Non-Steroidal/pharmacology , Combinatorial Chemistry Techniques , Esters , Molecular Structure , Peptides, Cyclic/chemistry , Peptides, Cyclic/pharmacology , StereoisomerismABSTRACT
A highly stereoselective total synthesis of (-)-tirandamycin C has been achieved following a desymmetrization protocol developed in our group, Horner-Wadsworth-Emmons olefination, acid-catalyzed ketalization, Still-Gennari (Z)-selective olefination, and Dieckmann cyclization as key reactions.
