Preparation of bioactive podolactones via a new Pd-catalysed bislactonisation reaction. Synthesis of oidiolactone C

Barrero, Alejandro F.; Moral, José F. Quı́lez del; Cuerva, Juan M.; Cabrera, Eduardo; Jiménez-González, David

doi:10.1016/s0040-4039(00)00815-7

Cited by 13 publications

(10 citation statements)

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“…A strong, negative cotton effect at 283 nm (in methanol) was consistent with the absolute configuration of LL-Z1271 (53) as shown 254. X-ray analysis of compound 51showed this molecule to contain the same relative configuration as LL-Z1271β (53) further confirming the close biosynthetic relationship between compounds 48-52 and compound 53 251,252,255. Absolute configurations for these compounds have been determined through various approaches, including stereoselective synthesis, derivatization, analysis of CD and crystal data, and comparison with the known absolute configurations of co-metabolites [251][252][253][254][255].…”

supporting

confidence: 52%

“…X-ray analysis of compound 51showed this molecule to contain the same relative configuration as LL-Z1271β (53) further confirming the close biosynthetic relationship between compounds 48-52 and compound 53 251,252,255. Absolute configurations for these compounds have been determined through various approaches, including stereoselective synthesis, derivatization, analysis of CD and crystal data, and comparison with the known absolute configurations of co-metabolites [251][252][253][254][255]. The fungicolous isolate chemically investigated in this study, MYC 1674 (= NRRL 46122), was identified as an isolate of Neofusicoccum parvum (anamorph = Botryosphaeria parva) after comparison of partial sequence analysis data with those in the GenBank database (www.ncbi.nlm.nih.gov/BLAST; 100% match with N. parvum) 89,263.…”

mentioning

confidence: 68%

“…Eventually, HMQC and HMBC data were used to assign the planar structure of A literature search for the structure shown in Figure 11 identified compound 48 as a synthetic intermediate in a process used for the preparation of oidiolactone C (49). 251 Although compound 48 has been previously described, this is the first report of its occurrence as a natural product. We propose the name oidiolactone G for 48, following in the name sequence of previously described members of this family of fungal metabolites.…”

Section: X-ray Crystallographic Analysis Of the P-iodobenzenesulfonylmentioning

confidence: 83%

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Chemical investigations of endophytitc and fungicolous fungi

Jordan¹

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Fungal infections of crops and humans are widespread, and the costs associated with their prevention and treatment highlight a need for new antifungal agents. In addition, increased antimicrobial resistance enhances the need for new classes of antibiotics. Fortunately, fungi themselves are a rich source of bioactive secondary metabolites, including some clinically useful antifungal agents. The role of fungi as decomposers sometimes results in these organisms being parasitic, mutualistic, or commensal with other organisms in their ecological communities. Such interspecies relationships are commonly associated with the production of biologically active compounds. The research described in this thesis involves studies of fungi from different ecological niches as part of an ongoing search for new bioactive natural products. Chapters 2-4 in this thesis describe investigations of secondary metabolites produced by selected fungal endophytes of corn. Endophytic fungi are those that grow in association with a plant host. Our group has previously reported the occurrence of antifungal pyrrocidines and phytotoxic dihydroresorcylide analogues from the maize-protective endophyte Acremonium zeae. The further studies discussed in this thesis describe bioactive secondary metabolites produced by isolates of three other endophytic fungal species. While vii

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confidence: 52%

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confidence: 68%

Section: X-ray Crystallographic Analysis Of the P-iodobenzenesulfonylmentioning

confidence: 83%

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Chemical investigations of endophytitc and fungicolous fungi

Jordan¹

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“…Related with the above-mentioned podolactone syntheses, the first synthesis of the antifungal oidiolactone C ( 69 ) was carried out from trans -communic acid ( 1 ) (Scheme 14) [96,97]. The key step of the synthesis is a new bislactonization reaction catalyzed by Pd(II), giving rise to the podolactone-type tetracyclic skeleton from a norlabdadienedioic acid.…”

Section: Use Of Communic Acids As Starting Materials For the Synthmentioning

confidence: 99%

Communic Acids: Occurrence, Properties and Use as Chirons for the Synthesis of Bioactive Compounds

et al. 2012

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Communic acids are diterpenes with labdane skeletons found in many plant species, mainly conifers, predominating in the genus Juniperus (fam. Cupresaceae). In this review we briefly describe their distribution and different biological activities (anti- bacterial, antitumoral, hypolipidemic, relaxing smooth muscle, etc.). This paper also includes a detailed explanation of their use as chiral building blocks for the synthesis of bioactive natural products. Among other uses, communic acids have proven useful as chirons for the synthesis of quassinoids (formal), abietane antioxidants, ambrox and other perfume fixatives, podolactone herbicides, etc., featuring shorter and more efficient processes.

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“…The dilactone oidiolactone C (102) was synthesized by Barrero et al [81]. Bendall et al [82] converted totarol into the nagilactone A analogue (103).…”

Section: Synthesismentioning

confidence: 99%

The Chemistry of Bioactive Diterpenes

Banerjee¹,

Laya²,

Mora³

et al. 2008

COC

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This article reviews the isolation, biological activity and syntheses of several diterpenes. The chemistry and biological activities of norditerpene dilactones have been described. The aim of the present article is to provide an overview on the important role of diterpenoid compounds in medicine and agriculture. The synthetic discussions of these diterpenes are very briefly described. Dedicated to Professor Kenji Mori for his valuable contributions to Terpene Chemistry.COOH Me Me OH Me Me H The Chemistry of Bioactive Diterpenes

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Preparation of bioactive podolactones via a new Pd-catalysed bislactonisation reaction. Synthesis of oidiolactone C

Abstract: A new route towards podolactone skeleton compounds, including the recently discovered Oidiolactone C, is described, using Pd-catalysed elimination of allylic tri¯uoroacetates and Pd-catalysed bislactonisation as key steps. #

Cited by 13 publications

References 13 publications

Chemical investigations of endophytitc and fungicolous fungi

Chemical investigations of endophytitc and fungicolous fungi

Communic Acids: Occurrence, Properties and Use as Chirons for the Synthesis of Bioactive Compounds

The Chemistry of Bioactive Diterpenes

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