Total Synthesis of Cyrneine A

Elamparuthi, Elangovan; Fellay, Cindy; Neuburger, Markus; Gademann, Karl

doi:10.1002/anie.201200515

Cited by 74 publications

(50 citation statements)

References 31 publications

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“…In the case of (R)-(−)-carvone), the corresponding alcohol (4a) was formed by reduction of the ketone functionality with lithium aluminium hydride. 22 The alcohol derivatives are obtained as single diasteromers in every case except for the limonene derivative (3a), which is obtained as a 1 : 1 mixture of diastereomers. 23 This simple but robust chemistry has allowed us to synthesise new terpene-based acrylic monomers in such a scale (50 g) that they can be polymerised (vide infra).…”

Section: Resultsmentioning

confidence: 99%

A facile and green route to terpene derived acrylate and methacrylate monomers and simple free radical polymerisation to yield new renewable polymers and coatings

et al. 2016

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A note on versions:The version presented here may differ from the published version or from the version of record. If you wish to cite this item you are advised to consult the publisher's version. Please see the repository url above for details on accessing the published version and note that access may require a subscription. We present new acrylic monomers derived directly from abundant naturally available terpenes via a facile, green and catalytic approach. These monomers can be polymerised to create new polymers with a wide range of mechanical properties that positions them ideally for application across the commodity and specialty plastics landscape; from packaging, cosmetic and medical, through to composites and coatings.We demonstrate their utility through formation of novel renewable polymer coatings.

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Section: Resultsmentioning

confidence: 99%

A facile and green route to terpene derived acrylate and methacrylate monomers and simple free radical polymerisation to yield new renewable polymers and coatings

et al. 2016

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“…[190] Intramolecular Heck coupling is used for the formation of the Robinson adduct 331. Despite rather harsh conditions (120°C) the yield obtained for this complex molecule is pretty good.…”

Section: Heck Reactionmentioning

confidence: 99%

Enantioselective Access to Robinson Annulation Products and Michael Adducts as Precursors

2017

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The Robinson annulation is a reaction that has been useful for numerous syntheses since its discovery in 1935, especially in the field of steroid synthesis. The products are usually obtained after three consecutive steps: the formation of an enolate (or derivative), a conjugate addition, and an aldol reaction. Over the years, several methodological improvements have been made for each individual step or alternative routes have been devised to access the Robinson annulation products. The first part of this Review outlines the most relevant developments towards the formation of monocarbonyl-derived Robinson annulation products (MRA products, MRAPs) and activated monocarbonyl-derived Robinson annulation products (AMRA products, AMRAPs). The following sections are then devoted to the diastereoselective and enantioselective synthesis of these products, while the last section describes the enantiomeric resolution of racemic mixtures.

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“…H), 7.09 (1H, s, arom. H), 6.14 (2H, s, -OCH 2 O-), 3.89 (3H, s,-OCH 3 ) (Kozawa et al, 1978b (d, C-2), 117.3 (t, C-9), 63.5 (d, C-5), 58.6 (d, C-4), 31.8 (t, C-6), 29.1 (t, C-3), 22.6 (q, C-7), 14.1 (q, C-10) (Elamparuthi et al, 2012 (Ikeda et al, 1998 ( Kuo et al, 1993).…”

Section: H and 13 C Nmr Spectra For Compounds 1-9mentioning

confidence: 99%