Concise synthesis of stagonolide-F by ring closing metathesis approach and its biological evaluation

Perepogu, Arun Kumar; Raman, D.; Murty, U. S. N.; Rao, V. Jayathirtha

doi:10.1016/j.bioorg.2008.12.002

Cited by 28 publications

(15 citation statements)

References 31 publications

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“…As shown in Fig. 5, this assumption was well documented in the synthesis of multiplolide A [47], herbarumins [79,[81][82][83][84][85], stagonolides [61,[86][87][88], aspinolide A [89], achaetolide [51,90,91], and the antimalarial nonenolide [92].…”

Section: Second the Selection Of Protecting Groups To Be Attached Tomentioning

confidence: 91%

“…Sch 642305 (57) [37]. Zone of inhibition results for antifungal activity revealed stagonolide F (20) had more than 80% activity against Aspergillus niger and more than 60% activity against Saccharomyces cereviseae, C. albicans and Rhizopus oryzae [86].…”

Section: Antifungal Activitymentioning

confidence: 98%

“…Sharpless AD [51,83,90,105,126,131,132] and Sharpless AE [64,86,88,[94][95][96][97]102,109,133,134] have been widely used to install the hydroxylated stereogenic centres.…”

Section: Sharpless Asymmetric Dihydroxylation (Ad) and Sharpless Asymmentioning

confidence: 99%

“…Jacobsen's HKR has been used frequently to form chiral epoxides, and when followed by epoxide homologation furnished the homoallylic alcohol with the required stereochemistry [86,89,90,94,95,102,131].…”

Section: Jacobsen's Hydrolytic Kinetic Resolution (Hkrmentioning

confidence: 99%

“…The total syntheses of the herbarumins I-III (40)(41)(42) [65][66][67][68][69]77,79,[81][82][83][84][85][103][104][105]128,131,133,139], microcarpalide (43) [70][71][72][73][74][75]81,108,[140][141][142][143][144][145][146], the stagonolides (17)(18)(19)(20)(21)(22)(23) and (44)(45) [61,64,[86][87][88]…”

Section: Examples Of Total Synthesismentioning

confidence: 99%

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Nonanolides of Natural Origin: Structure, Synthesis, and Biological Activity

Sun¹,

Lu²,

Ree³

et al. 2012

curr med chem

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Naturally occurring nonanolides (synonym decanolides) are a large family of secondary metabolites with an interesting 10- membered macrolide subunit. Metabolites of the nonanolide family have been found to have various biological activities, including cytotoxic, phytotoxic, antimalarial, antifungal, antibacterial, and antimicrofilament activities. An early review of the chemistry and bioactivity of nonanolides was presented in 1996, covering the literature published between 1975 and 1995. During the past decades, the broad spectrum of bioactivity and the intriguing structure of the medium-sized ring in nonanolide analogues have continuously drawn the attention of biologists and natural product and synthetic chemists, resulting in a great number of publications. This review summarizes in whole the recent progress in the field of the nonanolides of natural origin, aiming to give the readers a brief view of the compounds, concerning their natural occurrence, structural elucidation, biological activities, total synthesis, and structure-activity relationships. The article covers the literature published in the period from the beginning of 1996 to July 2011.

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Section: Second the Selection Of Protecting Groups To Be Attached Tomentioning

confidence: 91%

Section: Antifungal Activitymentioning

confidence: 98%

“…Sharpless AD [51,83,90,105,126,131,132] and Sharpless AE [64,86,88,[94][95][96][97]102,109,133,134] have been widely used to install the hydroxylated stereogenic centres.…”

Section: Sharpless Asymmetric Dihydroxylation (Ad) and Sharpless Asymmentioning

confidence: 99%

Section: Jacobsen's Hydrolytic Kinetic Resolution (Hkrmentioning

confidence: 99%

Section: Examples Of Total Synthesismentioning

confidence: 99%

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Nonanolides of Natural Origin: Structure, Synthesis, and Biological Activity

Sun¹,

Lu²,

Ree³

et al. 2012

curr med chem

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Enantioselektive allylische Hydroxylierung von ω‐Alkensäuren und ‐estern mittels der P450‐BM3‐Monooxygenase

Neufeld¹,

Henßen²,

Pietruszka³

2014

Angewandte Chemie

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Chirale Allylalkohole der w-Alkensäuren und entsprechende Derivate sind essentielle Bausteine für die Synthese biologisch aktiver Verbindungen. Die direkte enantioselektive C-H-Oxidation von linearen terminalen Olefinen ermçglicht den effizientesten Zugang zu diesen Strukturen. Synthetische Methoden für diese Umsetzungen stehen jedoch nur begrenzt zur Verfügung und liefern unzureichende Selektivitäten. Hier wird ein enzymatischer Ansatz zu diesen interessanten Zielverbindungen mittels der P450-BM3-Monooxygenase vorgestellt, der allylische Hydroxylierungen mit hohen bis exzellenten Chemo-und Enantioselektivitäten ermçglicht.

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Enantioselective Allylic Hydroxylation of ω‐Alkenoic Acids and Esters by P450 BM3 Monooxygenase

2014

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Chiral allylic alcohols of ω-alkenoic acids and derivatives thereof are highly important building blocks for the synthesis of biologically active compounds. The direct enantioselective C-H oxidation of linear terminal olefins offers the shortest route toward these compounds, but known synthetic methods are limited and suffer from low selectivities. Described herein is an enzymatic approach using the P450 BM3 monooxygenase mutant A74G/L188Q, which catalyzes allylic hydroxylation with high to excellent chemo- and enantioselectivities providing the desirable secondary alcohols.

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Concise synthesis of stagonolide-F by ring closing metathesis approach and its biological evaluation

Cited by 28 publications

References 31 publications

Nonanolides of Natural Origin: Structure, Synthesis, and Biological Activity

Nonanolides of Natural Origin: Structure, Synthesis, and Biological Activity

Enantioselektive allylische Hydroxylierung von ω‐Alkensäuren und ‐estern mittels der P450‐BM3‐Monooxygenase

Enantioselective Allylic Hydroxylation of ω‐Alkenoic Acids and Esters by P450 BM3 Monooxygenase

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