By Mario Waser
This ebook offers the reader with an illustrative evaluation pertaining to winning and favourite purposes of organocatalysis within the box of normal product synthesis. the focus might be on organocatalytic key-steps for every (multi-step) synthesis defined, while different frequently relatively leading edge alterations can be passed over, as this might be past the scope of this volume.
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Extra resources for Asymmetric Organocatalysis in Natural Product Syntheses
G. cycloadditions or conjugate additions). Furthermore, these are often stereoselective reactions that are otherwise hard to achieve in such an easy and general way as with the use of a simple chiral amine. Accordingly, this novel strategy has set the stage for the development of some extraordinarily short and straightforward syntheses of complex (natural) products. 1 Pericyclic Reactions Following the seminal report of MacMillan et al. in 2000 (27), several applications of iminium ion-activated Diels-Alder reactions in complex natural product syntheses have been reported, either carrying out the cyclization in an intra- or an intermolecular fashion.
The Takayama group has for several years been at the forefront in the synthesis of cernuane- and quinolizidine-type alkaloids (138–142). Recently, they developed a divergent strategy for the syntheses of 144–147 starting from the (+)-citronellal-derived aldehyde 148 (138, 139). Organocatalytic a-amination of 148 catalyzed by (R)-138 gave a rather labile amination product that was directly converted further to the stable oxazolidinone 149. Further modification then gave the key intermediate 150, which could be used to obtain cermizine C (144), cermizine D (145), and senepodine G (146), as well as cernuine (147) (Scheme 35).
N—O cleavage) for the conversion of the (S)-citronellol-derived aldehyde 132 to g-hydroxy-a,b-unsaturated ester 133 early in their 18-step first total synthesis of neosymbioimine (134) (116), a minor amphoteric metabolite of the symbiotic marine dinoflagellate Symbiodinium sp. (117) (Scheme 31). The synthesis of disparlure (135) represents yet another fine example for the high potential of enamine-catalyzed a-functionalizations of aldehydes in the synthesis of natural products. The enantiomer (+)-135 is a sex pheromone of the female gypsy 26 2 Enamine Catalysis 1.
Asymmetric Organocatalysis in Natural Product Syntheses by Mario Waser