Abstract
Abscisic acid (ABA) is a natural product, which is a well-known phytohormone. However, this molecule has recently exhibited interesting biological activities, emphasizing the need for a simple and direct access to new analogues based on the ABA framework. Our strategy relies on a pallado-catalyzed Mizoroki-Heck cross-coupling as key reaction performed in solvent and ligand free conditions. After a careful optimization, we succeeded in accessing various (E/Z)-dienes and (E/E/Z)-trienes in moderate to good yields without isomerization and applied the same approach to the synthesis of ABA in an environmentally sound manner.
Highlights
IntroductionPolyenic scaffolds scaffolds constitute constitutean animportant importantfunctionality functionalityamong amongorganic organiccompounds compoundsand andhave havePolyenic a a high synthetic interest since medicinally relevant molecules and natural products exhibit diene high synthetic interest since medicinally relevant molecules and natural products exhibit diene fragments (Figure (Figure 1) fragments 1) [1]. [1]
In our effort to develop environmentally benign tools [34,35,36], we report the use of the Mizoroki-Heck reaction, whichreaction requiresofsimple and directly accessible
1,3-rearrangement of the allylic alcohol, a transformation previously requires the use of a ligand, palladium supported catalyst, palladium nanocatalyst or microwave described by
Summary
(ABA) is is aanatural naturalproduct, product, which whichis isaawell‐known well-knownphytohormone. Abstract: this molecule molecule has has recently interesting biological activities, emphasizing emphasizing the the need need for for aa this recently exhibited exhibited interesting biological activities, simple and direct access to new analogues based on the ABA framework. Our strategy relies on aa simple and direct access to new analogues based on the ABA framework. Mizoroki-Heck cross-coupling as key reaction performed in solvent and ligand pallado‐catalyzed Mizoroki‐Heck cross‐coupling as key reaction performed in solvent and ligand free conditions. Optimization, we we succeeded succeeded in in accessing accessing various various (E/Z)-dienes (E/Z)‐dienes and (E/E/Z)-trienes in moderate to good yields without isomerization and applied the same approach to (E/E/Z)‐trienes in moderate to good yields without isomerization and applied the same approach to the synthesis synthesis of of ABA.
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