Stereoselective Total Synthesis of Xestodecalactone C

Rajesh, K.; Suresh, Vangaru; Selvam, J. Jon Paul; Rao, Chitturi Bhujanga; Venkateswarlu, Y.

doi:10.1002/hlca.200900068

Cited by 10 publications

(4 citation statements)

References 30 publications

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“…Other approaches used in the asymmetric synthesis of nonanolides are exemplified by the Katsuki-Sharpless epoxidation [82], Brown's asymmetric allylation [105], intermolecular NHK reaction [103], Grignard addition [77,139], Prins cyclization [84,121], stereoselective 1,3-syn reduction [85,123], and diastereoselective I 2 -induced electrophilic cyclization [122].…”

Section: Other Approachesmentioning

confidence: 99%

“…Introducing the chiral homoallylic alcohol or transforming to the required stereochemistry was often achieved by Keck asymmetric allylation [44,51,82,122,129] or by Mitsunobu inversion [84,87,91,104,116].…”

Section: Keck Asymmetric Allylation [135] and Mitsunobu Inversion [118]mentioning

confidence: 99%

“…Fujioka et al built the macrolactone via Corey-Mukaiyama lactonization [120]. Syntheses of xestodecalactones A-C (54-56) were described utilizing intramolecular Friedel-Crafts (IFC) acylation as the ringclosing step [46,48,49,[121][122][123]]. An intramolecular Diels-Alder approach was employed towards the construction of the macrocyclic lactone ring and the perhydrobenzofuran system of the colletofragarones [124].…”

Section: Other Specific Approachesmentioning

confidence: 99%

See 2 more Smart Citations

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: Other Approachesmentioning

confidence: 99%

Section: Keck Asymmetric Allylation [135] and Mitsunobu Inversion [118]mentioning

confidence: 99%

Section: Other Specific Approachesmentioning

confidence: 99%

See 1 more Smart Citation

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

Sun¹,

Lu²,

Ree³

et al. 2012

curr med chem

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“…The corresponding macrolide 362 was obtained in 40% yield via an intramolecular FC acylation reaction of the carboxylic acid 361 using CF 3 COOH/(CF 3 CO) 2 O 346 Finally, compound 362 was transformed into the desired natural product 346 after several steps ( Scheme 75 ). 362 …”

Section: Applications Of Friedel–crafts In Total Synthesis Of Natural...mentioning

confidence: 99%

Applications of Friedel–Crafts reactions in total synthesis of natural products

et al. 2018

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Cytospolides A–E, New Nonanolides from an Endophytic Fungus, Cytospora sp.

Kurtán

Yang

et al. 2011

Eur J Org Chem

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Cytospolides A-E (1-5), five new nonanolides with an unprecedented 15-carbon skeleton with the unique chemical feature of a C-2 methyl group, were isolated from the endophytic fungus Cytospora sp. The structures were elucidated by spectroscopic analysis, chemical interconversion, and single-crystal XRD. The solution and solid state conformers were compared by experimental methods (X-ray, NMR) and solvent and gas phase DFT calculations. The absolute configurations were assigned by time dependent (TD)-DFT calculations of CD spectra, including solution and solid state CD/

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Stereoselective Total Synthesis of Xestodecalactone C

Cited by 10 publications

References 30 publications

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

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

Applications of Friedel–Crafts reactions in total synthesis of natural products

Cytospolides A–E, New Nonanolides from an Endophytic Fungus, Cytospora sp.

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