Epoxide synthesis by ring closure - Organic Chemistry

F., III, Towards organo-click chemistry: Development of organocatalytic multicomponent reactions through combinations of Aldol, Wittig, Knoevenagel, Michael, Diels-Alder and Huisgen cycloaddition reactions.

In this tutorial, Sal and Jay show the SN1 and SN2 ring opening reactions of epoxides.

V.; Van der Eycken, E., A microwave-assisted click chemistry synthesis of 1,4-disubstituted 1,2,3-triazoles via a copper(I)-catalyzed three-component reaction.


Synthesis | Organic Synthesis | Chemical Reactions

T1 - SYNTHESIS AND ACID-CATALYZED AND BASE-CATALYZED REACTIONS OF HEXOBARBITAL 1',2'-EPOXIDE AND HEPTABARBITAL 1',2'-EPOXIDE

Stereoselective synthesis of the C24-C40 segment of aculeximycin has been achieved by using the Kobayashi aldol reactions and epoxy-opening rearrangement reactions. The C33-C40 segment was synthesized by the Kobayashi aldol reaction followed by epoxidation and Jung rearrangement of epoxide 9, while the C25-C32 segment was constructed by the Kobayashi aldol reaction followed by epoxidation and the epoxy-opening rearrangement reaction of epoxide 13. These segments were connected by the aldol reaction and the sequential dehydration, reduction, and conversion of ethyl ester to ethyl ketone to give the C24-C40 segment 1. All stereogenic centers were constructed by substrate-controlled stereoselective reactions.