Chemoenzymatic Synthesis of (+)-Asperpentyn and the Enantiomer of the Structure Assigned to Aspergillusol A

Lan, Ping; White, Lauren E.; Taher, Ehab S.; Guest, Prudence Elizabeth; Banwell, Martin G.; Willis, Anthony C.

doi:10.1021/acs.jnatprod.5b00304

Cited by 35 publications

(22 citation statements)

References 28 publications

(29 reference statements)

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“…Compounds 87 and 88 , representing the structures assigned to (+)‐asperpentyn and ent ‐aspergillusol A respectively, have also been prepared using Sonogashira cross‐coupling protocols and by such means the structures assigned to these natural products confirmed …”

Section: Synthetic Studies Involving Cross‐coupling and Related C−c Bmentioning

confidence: 99%

The Exploitation of Enzymatically‐Derived cis‐1,2‐Dihydrocatechols and Related Compounds in the Synthesis of Biologically Active Natural Products

Taher

Banwell

Buckler

et al. 2017

The Chemical Record

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The title compounds of the general form 1 can be produced at large scale and in essentially enantiomerically pure form (when X≠H) through the whole cell biotransformation of the corresponding aromatic. The "dense" and varied functionality associated with these metabolites mean that they have become increasingly useful chirons for the total synthesis of a range of natural product types. This personal account details the outcomes of a nearly three-decade long campaign within our group to exploit these compounds in the synthesis of a diverse range of small molecule natural product targets. The work is subdivided according to the key transformation(s) employed in each synthesis. The development of newer chirons that "complement" the utility of the cis-1,2-dihydrocatechols are also described.

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Section: Synthetic Studies Involving Cross‐coupling and Related C−c Bmentioning

confidence: 99%

The Exploitation of Enzymatically‐Derived cis‐1,2‐Dihydrocatechols and Related Compounds in the Synthesis of Biologically Active Natural Products

Taher

Banwell

Buckler

et al. 2017

The Chemical Record

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“…Conjugated enynes are prevalent structural motifs in a broad range of bioactive compounds, and also are versatile building blocks in synthetic chemistry . However, a general and completely selective strategy to access conjugated enynes remains challenging as the alkyne dimerization, and cross‐coupling strategies, would potentially result in the formation of a mixture of regio‐ and stereoisomers.…”

Section: Methodsmentioning

confidence: 99%

Selective Hydroarylation of 1,3‐Diynes Using a Dimeric Manganese Catalyst: Modular Synthesis of Z‐Enynes

et al. 2018

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The transition-metal-catalyzed selective hydroarylation of unsymmetrical alkynes represents the state-of-art in organic chemistry,and still mainly relies on the use of precious late-transition-metal catalysts.R eported herein is an unprecedented Mn I -catalyzed hydroarylation of unsymmetrical 1,3diyne alcohols with commercially available arylboronic acids with predictive selectivity.T his method addresses the challenges in regio-, stereo-, and chemoselectivity.I to ffers ag eneral, convenient and practical strategy for the modular synthesis of multisubstituted Z-configurated conjugated enynes. This protocol is distinguished by its operational simplicity, complete selectivity,e xcellent functional-group compatibility, and gram-scale potential. Ad imeric Mn I species,M n 2 -(CO) 8 Br 2 ,w as proven to be am uchm ore efficient catalyst precursor than Mn(CO) 5 Br. Scheme 1. Manganese(I)-catalyzed hydroarylation of alkynes and our design.

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“…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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Chemoenzymatic Synthesis of (+)-Asperpentyn and the Enantiomer of the Structure Assigned to Aspergillusol A

Cited by 35 publications

References 28 publications

The Exploitation of Enzymatically‐Derived cis‐1,2‐Dihydrocatechols and Related Compounds in the Synthesis of Biologically Active Natural Products

The Exploitation of Enzymatically‐Derived cis‐1,2‐Dihydrocatechols and Related Compounds in the Synthesis of Biologically Active Natural Products

Selective Hydroarylation of 1,3‐Diynes Using a Dimeric Manganese Catalyst: Modular Synthesis of Z‐Enynes

In Depth Natural Product Discovery from the Basidiomycetes Stereum Species

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