An Enantioselective Route to Paeonilactone A via Palladium- and Copper-Catalyzed Reactions

Jonasson, Catrin; Rönn, Magnus; Bäckvall, Jan‐E.

doi:10.1021/jo991787i

Cited by 36 publications

(19 citation statements)

References 32 publications

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“…In a demonstration of the synthetic utility of this oxidation, a key intermediate (174) in the synthesis of paenilactone A by Bäckvall and co-workers was constructed in two steps without compromising the enantiopurity (Scheme 75). [152] In 2004, Yokoyama et al described a protecting-groupfree total synthesis of the ergot alkaloid clavicipitic acid (177). [153] A chemoselective palladium-catalyzed Heck reaction/cyclization between 4-bromotryptophan (175) and 2-methyl-3-buten-2-ol (176) is the cornerstone of this synthesis (Scheme 76).…”

Section: Angewandte Chemiementioning

confidence: 99%

Chemoselectivity and the Curious Reactivity Preferences of Functional Groups

2009

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Achieving high levels of chemoselectivity has been the Achilles' heel of chemical synthesis. The excitement generated by the successful realization of chemoselective strategies underscores the painstaking efforts to define a set of conditions conducive to selection among the available reaction pathways. We discuss in this Review various aspects of chemoselectivity that have been addressed in a range of synthetic methods over the past decade. We have focused on the proposed mechanistic basis of the reactions under consideration in an attempt to categorize them and highlight the key concepts that have been emerging on the basis of these studies. Our overview of recent advances in chemoselective processes suggests that significant progress has been made, but a lot of challenges lie ahead.

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Section: Angewandte Chemiementioning

confidence: 99%

Chemoselectivity and the Curious Reactivity Preferences of Functional Groups

2009

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“…We synthesized diene 4 in racemic form and as separate enantiomers from the corresponding 2,4-cyclohexadienylacetic acids [9] (Supporting Information). The reactions were monitored by 1 H NMR spectroscopy and evaluated by using our SimFit program.…”

mentioning

confidence: 99%

Systems Chemistry: Kinetic and Computational Analysis of a Nearly Exponential Organic Replicator

et al. 2005

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In 1997, Wang and Sutherland reported a case of selfreplication in a Diels-Alder reaction.[1] This system is remarkable for at least two reasons: it constituted the first example of nearly exponential growth and it had the potential to exhibit two kinds of self-replication, homochiral autocatalysis and heterochiral cross-catalysis, because a chiral diene was employed. Unfortunately, the authors could not complete a stereochemical analysis of their system. We report herein mechanistic and stereochemical studies of variants of the Wang-Sutherland replicator. We show that only one of four potential diastereomers is formed within our detection limits and that this diastereomer is involved in both autocatalytic and cross-catalytic channels. A computational study suggests that the system can be classified as an example of a nearby

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“…The 13 C NMR (DEPT) spectrum displayed ten carbons ascribed to two quaternary carbons, four methines, two methylenes and two methyls. Careful analyses of its 1D and 2D NMR data indicated that compound 1 was a stereoisomer of 5,6-dihydroxy-3,6-dimethylhexahydrobenzofuran-2-one [28] but a different stereochemistry at C-6, which was supported by X-ray diffraction ( Fig. 4).…”

Section: Resultsmentioning

confidence: 81%