A 4+3 Cycloaddition Approach to the Synthesis of (±)-Sterpurene

Harmata, Michael; Bohnert, Gary

doi:10.1021/ol027176l

Cited by 54 publications

(16 citation statements)

References 34 publications

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“…Their approach used a strategy in which α,β-unsaturated enone moiety of an electron-withdrawing β-substituent promotes an intermolecular [2+2]-photocycloadditionm, which may provide further applications in the synthesis of analogs [ 22 ]. Harmata synthesized (±)-sterpurene using a [4+3] cycloaddition approach including a (4 + 3) cycloaddition reaction and a quasi-Favorskii rearrangement [ 49 ]. The chemoenzymatic total synthesis of 4,12-dihydroxysterpurene (84) and its enantiomer has also been reported [ 50 ].…”

Section: Secondary Metabolites From Stereum Andmentioning

confidence: 99%

In Depth Natural Product Discovery from the Basidiomycetes Stereum Species

Tian

Zhao

et al. 2020

Microorganisms

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Natural metabolites from microorganisms play significant roles in the discovery of drugs, both for disease treatments in humans, and applications in agriculture. The Basidiomycetes Stereum genus has been a source of such bioactive compounds. Here we report on the structures and activities of secondary metabolites from Stereum. Their structural types include sesquiterpenoids, polyketides, vibralactones, triterpenoids, sterols, carboxylic acids and saccharides. Most of them showed biological activities including cytotoxic, antibacterial, antifungal, antiviral, radical scavenging activity, autophagy inducing activity, inhibiting pancreatic lipase against malarial parasite, nematocidal and so on. The syntheses of some metabolites have been studied. In this review, 238 secondary metabolites from 10 known species and various unidentified species of Stereum were summarized over the last seven decades.

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Section: Secondary Metabolites From Stereum Andmentioning

confidence: 99%

In Depth Natural Product Discovery from the Basidiomycetes Stereum Species

Tian

Zhao

et al. 2020

Microorganisms

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“…experiment proved promising. Diene 43 was in our lab due to our sterpurene work 37 and was perfect for proof-ofprinciple.…”

Section: Account Syn Lettmentioning

confidence: 99%

Fun with (4+3)-Cycloadditions

Harmata

2018

Synlett

Self Cite

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This account describes how I began my adventure in the area of (4+3)-cycloadditions and then focuses on two ongoing projects: a new catalytic asymmetric (4+3)-cycloaddition and what might be described as the ‘rebirth’ of oxidopyridinium ion (4+3)-cycloaddition chemistry. References to other people’s work are made where appropriate.1 Introduction2 Asymmetric, Catalytic (4+3)-Cycloadditions3 Oxidopyridinium Ions and (4+3)-Cycloadditions4 Conclusions and the Future

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“…27,28,55 Chromium(VI) oxide-3,5-dimethylpyrazole has also been found to be the reagent of choice in many natural product total syntheses because it has a good functional group tolerance. [59][60][61][62][63] Illustrative examples are depicted in Scheme 7 with the oxidation of olefin 34 to enone 35, which is an intermediate in the synthesis of sterpurene (36), 64 and the oxidation of the highly functionalized alkene 37 to enone 38, an intermediate for manzamine A. 65 In both cases, several other oxidants had been tried without success.…”

Section: Figure 1 Amine Complexes Of Chromium(vi) Reagentsmentioning

confidence: 99%

Allylic Oxidations of Olefins to Enones

Weidmann

Maison

2013

Synthesis

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Allylic oxidations of olefins to enones are C-H functionalizations and are valuable organic transformations that permit the synthesis of value-added products from simple precursors. A variety of stoichiometric and catalytic metal-based methods are available for these conversions. In addition, metal-free and biocatalytic protocols are gaining in importance. This review summarizes the available oxidation methods and compares their regio-and chemoselectivities.

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A 4+3 Cycloaddition Approach to the Synthesis of (±)-Sterpurene

Abstract: A synthesis of the sesquiterpene sterpurene is presented. Key steps include a 4+3 cycloaddition reaction and a quasi-Favorskii rearrangement. [reaction--see text]

Cited by 54 publications

References 34 publications

In Depth Natural Product Discovery from the Basidiomycetes Stereum Species

In Depth Natural Product Discovery from the Basidiomycetes Stereum Species

Fun with (4+3)-Cycloadditions

Allylic Oxidations of Olefins to Enones

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