Synthesis of densely functionalized enantiopure indolizidines by ring-closing metathesis (RCM) of hydroxylamines from carbohydrate-derived nitrones.

ABSTRACT:

Background

Indolizidine alkaloids widely occur in nature and display interesting biological activity. This is the reason for which their total synthesis as well as the synthesis of non-natural analogues still attracts the attention of many research groups. To establish new straightforward accesses to these molecules is therefore highly desirable.

Results

The ring closing metathesis (RCM) of enantiopure hydroxylamines bearing suitable unsaturated groups cleanly afforded piperidine derivatives in good yields. Further cyclization and deprotection of the hydroxy groups gave novel highly functionalized indolizidines. The synthesis of a pyrroloazepine analogue is also described.

Conclusion

We have developed a new straightforward methodology for the synthesis of densely func

SUBMITTER: Bonanni M 

PROVIDER: S-EPMC2151072 | biostudies-literature | 2007 Dec

REPOSITORIES: biostudies-literature