An unusual oxidative cyclization. A synthesis and absolute stereochemical assignment of (-)-rocaglamide

Trost, Barry M.; Greenspan, Paul D.; Yang, Benhui; Saulnier, Mark G.

doi:10.1021/ja00180a081

Cited by 105 publications

(71 citation statements)

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“…Compound 49 was then further functionalized to the previously reported intermediate 41 , which had been previously converted to (+)-methyl rocaglate ( 42 ) by both Trost and Frontier. 51,52 …”

Section: Update On Synthetic Methods For Cyclopenta[b]benzofuransmentioning

confidence: 99%

Rocaglamide, silvestrol and structurally related bioactive compounds from Aglaia species

et al. 2014

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Investigations on the chemistry and biology of rocaglamide, silvestrol and structurally related bioactive compounds from Aglaia species during the period 2006–2013 are reviewed. Included are new phytochemical studies of naturally occurring rocaglamide derivatives, an update on synthetic methods for cyclopenta[b]benzofurans, and a description of the recent biological evaluation and mechanism-of-action studies on compounds of this type.

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Section: Update On Synthetic Methods For Cyclopenta[b]benzofuransmentioning

confidence: 99%

Rocaglamide, silvestrol and structurally related bioactive compounds from Aglaia species

et al. 2014

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“…152 Using an enantiomeric synthetic procedure, Trost et al determined the absolute configuration of (−)-rocaglamide ( 58 ) as (1 R ,2 R ,3 S ,3a R ,8b S ) in 1990. 153 Spectroscopic data for this cyclopenta[ b ]benzofuran derivative were first published by Isman and Towers in 1993, who also showed rocaglamide to exhibit potent insecticidal activity against two variegated cutworms. 154 Since this initial work, more than 100 rocaglate derivatives have been isolated from some 35 Aglaia species.…”

Section: Potential Cancer Chemotherapeutic Agents From Selected Tropimentioning

confidence: 97%

The Relevance of Higher Plants in Lead Compound Discovery Programs

et al. 2011

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Along with compounds from terrestrial microorganisms, the constituents of higher plants have provided a substantial number of the natural product-derived drugs used currently in western medicine. Interest in the elucidation of new structures of the secondary metabolite constituents of plants has remained high among the natural products community over the first decade of the 21st century, particularly of species that are used in systems of traditional medicine or are utilized as botanical dietary supplements. In this review, progress made in the senior author’s laboratory in research work on naturally occurring sweeteners and other taste-modifying substances and on potential anticancer agents from tropical plants will be described.

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“…Following Trost's total synthesis of rocaglamide (1) in 1990 [11], more than ten different synthetic approaches have been developed, attesting to the fascination with these highly compact, functionalized heterocycles. Flavagline synthesis remains a challenge as the compounds have two contiguous quaternary chiral centers and cis aryl groups on adjacent carbons of a strained cyclopentane ring.…”

Section: Synthesesmentioning

confidence: 99%

“…Compound 18, which encompasses the critical features of flavaglines, was transformed in six steps into dehydroflavagline (19), which has been shown to yield methyl rocaglate in two steps by Trost [11].…”

Section: Synthesesmentioning

confidence: 99%

Flavaglines: Potent Anticancer Drugs that Target Prohibitins and the Helicase eIF4A

et al. 2013

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Flavaglines are complex natural products that are found in several medicinal plants of Southeast Asia in the genus Aglaia; these compounds have shown exceptional anticancer and cytoprotective activities. This review describes the significance of flavaglines as a new class of pharmacological agents and presents recent developments in their synthesis, structure-activity relationships, identification of their molecular targets and modes of action. Flavaglines display a unique profile of anticancer activities that are mediated by two classes of unrelated proteins: prohibitins and the translation initiation factor eIF4A. The identification of these molecular targets is expected to accelerate advancement toward clinical studies. The selectivity of cytotoxicity towards cancer cells has been shown to be due to an inhibition of the transcription factor HSF1 and an upregulation of the tumor suppressor TXNIP. In addition, flavaglines display potent anti-inflammatory, cardioprotective and neuroprotective activities; however, the mechanisms underlying these activities are yet to be elucidated.

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An unusual oxidative cyclization. A synthesis and absolute stereochemical assignment of (-)-rocaglamide

Cited by 105 publications

References 0 publications

Rocaglamide, silvestrol and structurally related bioactive compounds from Aglaia species

Rocaglamide, silvestrol and structurally related bioactive compounds from Aglaia species

The Relevance of Higher Plants in Lead Compound Discovery Programs

Flavaglines: Potent Anticancer Drugs that Target Prohibitins and the Helicase eIF4A

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