Synthesis of the carbon skeleton of the griseorhodins

Atkinson, Darcy J.; Furkert, Daniel P.; Brimble, Margaret A.

doi:10.1016/j.tet.2014.11.030

Cited by 3 publications

(2 citation statements)

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“…Interest in the synthesis of this natural product family has led the Brimble group to apply their synthetic strategy developed for the formal synthesis of (AE)-g-rubromycin (3) 57 to the griseorhodins. 78 Unlike g-rubromycin (3) the griseorhodins contain a methyl group at C-7 of the isocoumarin as opposed to a methyl ester and they endeavoured to exploit this functionality difference to establish a synthetic route to this subclass of rubromycin-based natural products (Scheme 45). Their previous determined that the lactone functional group was the key structure that prevented successful acid-mediated spirocyclisation of these substrates.…”

Section: Formal Synthesis Of (Ae)-g-rubromycin By LI Et Almentioning

confidence: 99%

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Isolation, biological activity, biosynthesis and synthetic studies towards the rubromycin family of natural products

Atkinson

Brimble

2015

Nat. Prod. Rep.

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The rubromycins are an ever growing family of natural products isolated from various Actinomycetes over the last 60 years. Exhibiting a highly attractive array of antimicrobial and enzyme activity, this unique family of compounds have attracted significant attention from many synthetic chemists. Investigations into the synthesis of the densely functionalised hexacyclic ring system have revealed many hidden synthetic challenges. This review covers the isolation, the reported biological activity and the detailed synthetic studies towards these complex natural products.

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Section: Formal Synthesis Of (Ae)-g-rubromycin By LI Et Almentioning

confidence: 99%

“…78 Scheme 48 Synthesis of ketone 234 and attempted spirocyclisation. 78 Scheme 49 Synthesis of isocoumarin precursors 236-238. 78…”

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Isolation, biological activity, biosynthesis and synthetic studies towards the rubromycin family of natural products

Atkinson

Brimble

2015

Nat. Prod. Rep.

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An Efficient Synthesis of 6‐oxa‐spiro[3.4]octan‐1‐one Derivates Through 3‐diazochroman‐4‐one and Alkene

Xiao

Zhang

et al. 2018

Adv Synth Catal

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Spiro[2,bicyclo [4.2.0]octane]-7'-one with fused and spirocyclic oxygen-containing rigid skeleton structure is obtained via Wolff rearrangement and cycloaddition with good yields. Then Spiro[2,2-dimethyl-benzofuran,hexahydro-isobenzofuran]-7'-one is synthesized by further Baeyer-Villiger oxidation. These two kinds of products have a special fused and spirocyclic oxygen-containing rigid skeleton structure and are reported by our group.

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