A Protecting Group Free Synthesis of (±)-Neostenine via the [5 + 2] Photocycloaddition of Maleimides

Lainchbury, Michael; Medley, Marcus I; Taylor, Piers M.; Hirst, Paul R.; Döhle, Wolfgang; Booker‐Milburn, Kevin I.

doi:10.1021/jo801108h

Cited by 95 publications

(38 citation statements)

References 52 publications

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“…This FEP reactor was essential for the protecting-group-free synthesis of (±)-neostenine [80]. The key step utilised the [5 + 2] cycloaddition (Scheme 27) for the construction of the pyrrolo[1,2- a ]azepine core 83 .…”

Section: Reviewmentioning

confidence: 99%

Flow photochemistry: Old light through new windows

Knowles

Elliott²,

Booker‐Milburn³

2012

Beilstein J. Org. Chem.

374

190

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SummarySynthetic photochemistry carried out in classic batch reactors has, for over half a century, proved to be a powerful but under-utilised technique in general organic synthesis. Recent developments in flow photochemistry have the potential to allow this technique to be applied in a more mainstream setting. This review highlights the use of flow reactors in organic photochemistry, allowing a comparison of the various reactor types to be made.

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Section: Reviewmentioning

confidence: 99%

Flow photochemistry: Old light through new windows

Knowles

Elliott²,

Booker‐Milburn³

2012

Beilstein J. Org. Chem.

374

190

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“…Stemona alkaloids 1-3 have been the targets of successful synthetic campaigns by this (24)(25)(26) and other groups (27)(28)(29)(30)(31)(32)(33)(34)(35)(36)(37), although the synthesis of neotuberostemonine 4 has yet to be realized. Our own interest in this class of natural products was driven initially by the challenges presented by these alkaloids in such a total synthesis context.…”

mentioning

confidence: 99%

Synthesis and receptor profiling ofStemonaalkaloid analogues reveal a potent class of sigma ligands

Frankowski

Setola²,

Evans³

et al. 2011

Proc. Natl. Acad. Sci. U.S.A.

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Reported biological activities of Stemona natural products, such as antitussive activity, inspired the development of synthetic methods to access several alkaloids within this family and in so doing develop a general route to the core skeleta shared by the class of natural products. The chemistry was subsequently adapted to afford a series of analogue sets bearing simplified, diverse Stemona -inspired skeleta. Over 100 of these analogues were subjected to general G protein-coupled receptor profiling along with the known antitussive compound, neostenine; this led to the identification of hit compounds targeting several receptor types. The particularly rich hit subset for sigma receptors was expanded with two focused library sets, which resulted in the discovery of a fully synthetic, potent chemotype of sigma ligands. This collaborative effort combined the development of synthetic methods with extensive, flexible screening resources and exemplifies the role of natural products in bioactivity mining.

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“…A similar [5 + 2] intramolecular cycloaddition was carried out in the multistep, protective group-free synthesis of alkaloid (±)-neostenine that took place in 9.5% yield over 14 steps. 35 The seminal work described above served as the archetype for the development of a plethora of related reactors employing medium pressure Hg vapor lamps. Since these light sources are known to generate much heat during process illumination, the temperature of the reactor at tubing surface was usually controlled by a thermometer affixed to the coils.…”

Section: Its All Around You: Flow Photoreactors With Internal Irradiamentioning

confidence: 99%