Asymmetric synthesis of apratoxin D via ACC ,-bisalkylation.
T1 - Asymmetrical radiation pattern synthesis of a linear array antenna by a least mean square method
Synthesis of asymmetrical multiantennary human milk oligosaccharides
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Denticulatins A and B are one of several polyketide-based natural products that have been synthesized using a SAMP/RAMP hydrazone alkylation as a key step (Scheme A). The denticulatins are intriguing polypropionate metabolites isolated from Siphonaria denticulata, a class of air-breathing mollusks. Denticulatins A and B were first isolated from these mollusks in 1983 off the coast of New South Wales, Australia. Although other marine isolates of similar biogenetic origin have antimicrobial properties, the biological function of the denticulatins is unknown. In 1989, Ziegler and Becker reported on the asymmetric total synthesis of (−)-denticulatins A and B starting from RAMP hydrazone . Alkylation of with allylic iodide , followed by copper (II) acetate-mediated hydrolysis, gave alkyl ketone in modest yield and with an ee of 89%.
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Another synthetic application of the ACC methodology has led to the first asymmetric total synthesis of apratoxin D (, Scheme ). Apratoxin D was recently isolated from two species of cyanobacteria, Lyngbya majuscula and Lyngbya sordida. It exhibits highly potent in vitro cytotoxicity against H-460 human lung cancer cells with an IC50 value of 2.6 nM. In this total synthesis, asymmetric ACC ,-bisalkylation was used as a means of establishing the insulated C-37 stereogenic center.
Wengryniuk et al. have used ACC-mediated asymmetric ,-bisalkylation for the enantiodivergent formal synthesis of both (R)- and (S)-stigmolone, wherein the same auxiliary is used to produce both enantiomers (Scheme ). Stigmolone is a highly potent pheromone secreted by the myxobacterium Stigmatella aurantica, which induces the formation of fruiting bodies.
Asymmetrical synthesis of lysine derivatives | …
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Despite its usefulness and widespread application, enolate chemistry is inherently complex because multiple reaction pathways, in addition to the desired one, may be possible for a given transformation. As a result, numerous challenges have had to be overcome in developing effective asymmetric -alkylation methods. For instance, in the case of carboxylate, aldehyde, and symmetrical ketone derivatives, a general and widely applicable asymmetric method has to control aspects of the reaction, including the geometry about the carbon–carbon bond of the enolate, as well as the facial approach of the electrophile to the enolate. In the case of nonsymmetrical ketones, the situation is even more complex as the regioselectivity of deprotonation must also be controlled. Given these inherent challenges, early asymmetric methods suffered from low selectivity and limitations with regard to the nature of the alkylating agent that could be used. However, building on those pioneering studies, the field has undergone significant advancement and highly selective asymmetric methods are now available for the -alkylation of carbonyl compounds, and these have found wide application in the asymmetric total synthesis of natural products.
Synthesis of 1,3,4-oxadiazoles - Organic Chemistry Portal
In what follows, a brief overview of the current state-of-the-art approaches to asymmetric -alkylation of carbonyl compounds is presented. This review is not intended to be comprehensive but to focus on the most established methods currently available—with historical context provided as necessary—and their practical applications in the context of natural products synthesis.
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