From Labdanes to Drimanes. Degradation of the Side Chain of Dihydrozamoranic Acid.

Rodilla, Jesús M.; Dı́ez, David; Urones, Julio G.; Rocha, Pedro M.

doi:10.3390/90500300

Cited by 6 publications

(2 citation statements)

References 22 publications

(15 reference statements)

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“…We then proceeded to synthesize the key intermediate amide 4 (Scheme ). Although it was anticipated that the α,β-unsaturated ester in 20 would provide facile access to the corresponding epoxide in 21 , the treatment of substrate 21 with a variety of different oxidative agents, such as tert -butyl hydroperoxide (TBHP)/1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), m -chloroperbenzoic acid ( m -CPBA), and H 2 O 2 /NaOH, did not result in the formation of the desired product.…”

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confidence: 76%

Asymmetric Total Synthesis of (+)-Fusarisetin A via the Intramolecular Pauson–Khand Reaction

et al. 2013

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An asymmetic total synthesis of (+)-fusarisetin A has been achieved. The essential to our strategy was the application of the intramolecular Pauson-Khand reaction for the stereoselective construction of the trans-decalin subunit of (+)-fusarisetin A with a unique C16 quarternary chiral center. The developed chemistry offers an alternative to the IMDA reaction that has been used for fusarisetin A, and is applicable to analogue synthesis for biological evaluation.

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confidence: 76%

Asymmetric Total Synthesis of (+)-Fusarisetin A via the Intramolecular Pauson–Khand Reaction

et al. 2013

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“…The synthesis of sesquiterpenoids from labdane diterpenoids has also been reported [15]. On the other hand, degradations in the side chain of dihydrozamoranic acid were used for the synthesis of drimane [16]. Another important group of chemical reactions which included degradations in the side chain of (-)-sclareol, are those that allowed the preparation of terpenic synthons used in the synthesis of terpenylquinones with antitumoral activities such as (+)-puupehenone [17], chromazonarol and related compounds [18].…”

Section: Introductionmentioning

confidence: 99%

Oxidative Degradations of the Side Chain of Unsaturated Ent-labdanes. Part I.

et al. 2007

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Norrish Type II Reaction

2010

Comprehensive Organic Name Reactions and Reagents

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The light initiated intramolecular abstraction of a δ‐hydrogen of an excited ketone or aldehyde to generate a 1,4‐biradical, from which different products can form, including alkene, enol, and cyclobutanol and this reaction is generally known as the Norrish type II reaction. This reaction is also called as the Yang reaction. The study finds that this reaction is influenced by both environmental and structural factors. In addition, it is found that both the excited singlet (S1) and triplet (T1) state of a dialkyl ketone can undergo such reaction, whereas an aryl alkyl thioketone proceeds from the excited triplet state (T1), and the reaction of an ester primarily involves the excited triplet (T1). For aliphatic or benzylic hydrogen abstraction, ketones with a lowest π‐π * triplet state are much less reactive than those with the lowest n‐π * triplet state. The mechanism of the reaction for an aryl ketone and special ketones has been discussed. This reaction has been applied in organic synthesis, especially for the generation of free radicals.

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From Labdanes to Drimanes. Degradation of the Side Chain of Dihydrozamoranic Acid.

Abstract: Abstract:A new route for the degradation of the saturated side chain of dihydrozamoranic acid has been devised, giving an advanced intermediate, compound 14, useful for the synthesis of insect antifeedants such as warburganal and polygodial.

Cited by 6 publications

References 22 publications

Asymmetric Total Synthesis of (+)-Fusarisetin A via the Intramolecular Pauson–Khand Reaction

Asymmetric Total Synthesis of (+)-Fusarisetin A via the Intramolecular Pauson–Khand Reaction

Oxidative Degradations of the Side Chain of Unsaturated Ent-labdanes. Part I.

Norrish Type II Reaction

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