Abstract
The stereoselective synthesis of the (Z)-enamide fragment of chondrochloren (1) is described. A Buchwald-type coupling between amide 3 and (Z)-bromide 4 was used to generate the required fragment. The employed amide 3 comprising three chiral centers was obtained through a seven-step sequence starting from ᴅ-ribonic acid-1,4-lactone. The (Z)-vinyl bromide 4 is accessible in four steps from 4-hydroxybenzaldehyde. The pivotal cross coupling between both fragments was achieved after extensive experimentation with copper(I) iodide, K2CO3 and N,N′-dimethylethane-1,2-diamine.
Highlights
In the course of our program to provide synthetic access to biologically active natural products we targeted complex polyketides and depsipetides [1,2,3,4,5,6,7,8,9,10]
We report our investigations on the construction of the segments 3 and 4 as well as our results on the cross coupling between both fragments
The synthesis of the amide 3 started with TIPDS-protection of commercially available ᴅ-ribonic acid-1,4-lactone (5) (Scheme 1)
Summary
In the course of our program to provide synthetic access to biologically active natural products we targeted complex polyketides and depsipetides [1,2,3,4,5,6,7,8,9,10]. The stereoselective synthesis of the (Z)-enamide fragment of chondrochloren (1) is described. A Buchwald-type coupling between amide 3 and (Z)-bromide 4 was used to generate the required fragment. One particular group of compounds of particular focus in our research activities are natural products with enamide moieties [11].
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