The first total synthesis of putaminoxin and determination of its absolute configuration

Sabitha, Gowravaram; Kurra, Yadagiri; Swapna, R.; Yadav, J. S.

doi:10.1016/j.tetlet.2009.07.055

Cited by 20 publications

(18 citation statements)

References 3 publications

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“…NMR spectroscopy in combination with X-ray crystal structure analyses, Mosher's method, [ ] D values, CD, or quantum chemical CD calculations were extensively used in the elucidation of the relative and absolute configurations of nonanolides. In some cases, the absolute stereochemistry of nonanolides, for example putaminoxin (35) [44], mueggelone (39) [45], sporostatin (53) [46], multiplolide A (4) [47], xestodecalactones A, B and C (54)(55)(56) [48][49][50], and achaetolide (49) [41,51] were established by stereoselective total synthesis. The nonanolide class of metabolites is classified according to the previously established criteria: (i) simple nonanolides with methyl and oxygen substituents (Fig.…”

Section: Structures and Classification Of Nonano-lidesmentioning

confidence: 99%

“…Stagonospora cirsii Davis, a fungal pathogen isolated from Cirsium arvense (commonly called Canada thistle) and proposed as a potential mycoherbicide of this perennial noxious weed, produced phytotoxic metabolites both in liquid and solid cultures. Stagonolide A (44), the main phytotoxic metabolite with interesting phytotoxic properties, was isolated and characterized in 2007 [32]. From the same fungus grown in solid culture, eight additional new nonenolides, stagonolides B-I (45,(17)(18)(19)(20)(21)(22)(23) and modiolide A (8) were isolated.…”

Section: Simple Nonanolides With Methyl and Oxygen Substituentsmentioning

confidence: 99%

“…Their structures were characterized, using spectroscopic and chemical methods, as new nonanolides with a propyl or pentyl group at the C-9 position [15][16][17]. The absolute configuration was established by a total synthesis [44]. Mueggelone (39) was first isolated from a bloom-forming cyanobacterium of Aphanizomenon flos-aquae (Nostocaceae) [8].…”

Section: Nonanolides With Extended Alkyl Chainsmentioning

confidence: 99%

“…The absolute stereochemistry of 49 was established to be 3S,6R,7S,9R by way of relative stereochemical assignment with 1 H NMR analyses employing the corresponding acetonide, and determination of C3 and C9 stereochemistries by an extended Mosher's method [41]. Additionally, several fungal nonanolides are cheracterized with an n-propyl group at C-9, for example, the stagonolides A and B (44,45) [32,33], the putaminoxins A and E (35,38) [15][16][17], and the herbarumins I-III (40)(41)(42) [21,22].…”

Section: Nonanolides With Extended Alkyl Chainsmentioning

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%

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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: Structures and Classification Of Nonano-lidesmentioning

confidence: 99%

Section: Simple Nonanolides With Methyl and Oxygen Substituentsmentioning

confidence: 99%

Section: Nonanolides With Extended Alkyl Chainsmentioning

confidence: 99%

Section: Nonanolides With Extended Alkyl Chainsmentioning

confidence: 99%

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

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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Olefin Ring‐Closing Metathesis

Yet

2016

Organic Reactions

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The olefin ring‐closing metathesis reaction catalyzed by ruthenium and molybdenum complexes has been employed in the syntheses of carbocycles, heterocycles, supramolecular compounds, and in tandem metathesis reactions. Chiral ruthenium and molybdenum catalysts have provided high enantiomeric and diastereomeric excesses in ring‐closing metathesis reactions. Many of the unsuccessful medium‐ and large‐sized ring formations which were unsuccessful by traditional methods, such as the intramolecular Wittig, Horner–Wadsworth–Emmons, and Julia–Kocienski reactions, can now be formed by olefin ring‐closing metathesis reactions. Ring‐closing metathesis has been a key step and sometimes the only successful method for the synthesis of numerous natural products and drug discovery targets. The objective of this chapter is to provide an updated, comprehensive coverage of the literature of the olefin ring‐closing metathesis reaction and related processes. Key mechanistic points are summarized.

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