Abstract
A novel stereocontrolled approach has been developed for the syntheses of tashiromine and epitashiromine alkaloids from cyclooctene β-amino acids. The synthetic concept is based on the azetidinone opening of a bicyclic β-lactam, followed by oxidative ring opening through ring C–C double bond and reductive ring-closure reactions of the cis- or trans-cyclooctene β-amino acids.
Highlights
Indolizidine alkaloids are an important class of naturally occurring compounds which have received considerable attention as a result of their valuable physiological properties
We describe here a novel access route for the synthesis of tashiromine and epitashiromine by starting from an unsaturated bicyclic β-lactam
The retrosynthetic concept of the synthesis is represented on Scheme 1 and was based on the lactam ring opening, in continuation followed by oxidative ring opening of the formed β-amino esters and by reductive ring closure as key steps
Summary
Indolizidine alkaloids are an important class of naturally occurring compounds which have received considerable attention as a result of their valuable physiological properties. The retrosynthetic concept of the synthesis is represented on Scheme 1 and was based on the lactam ring opening, in continuation followed by oxidative ring opening of the formed β-amino esters and by reductive ring closure as key steps. Amino ester (±)-4 was subjected through its vicinal diol moiety to oxidative ring opening with NaIO4 in Scheme 1: Retrosynthesis of tashiromine and epitashiromine.
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