Total Synthesis of (−)‐Jiadifenin

Yang, Yang; Fu, Xingnian; Chen, Jianwei; Zhai, Hongbin

doi:10.1002/ange.201203176

Cited by 23 publications

(10 citation statements)

References 51 publications

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“…Allene is another frequently used olefin component, which shows not only high HH selectivity but offers further options for functionalization. Examples can be found in the synthesis of (±)-jiadifenin by Zhai and co-workers 312 and in a new route for the construction of the AB-ring core of taxol by the Kakiuchi group. 313 …”

Section: Direct Excitation and Sensitizationmentioning

confidence: 99%

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

et al. 2016

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The [2 + 2] photocycloaddition is undisputedly the most important and most frequently used photochemical reaction. In this review, it is attempted to cover all recent aspects of [2 + 2] photocycloaddition chemistry with an emphasis on synthetically relevant, regio-, and stereoselective reactions. The review aims to comprehensively discuss relevant work, which was done in the field in the last 20 years (i.e., from 1995 to 2015). Organization of the data follows a subdivision according to mechanism and substrate classes. Cu(I) and PET (photoinduced electron transfer) catalysis are treated separately in sections 2 and 4, whereas the vast majority of photocycloaddition reactions which occur by direct excitation or sensitization are divided within section 3 into individual subsections according to the photochemically excited olefin.

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Section: Direct Excitation and Sensitizationmentioning

confidence: 99%

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

et al. 2016

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“…To obtain vicinal quaternary-quaternary arrays and accomplish the total synthesis of several natural products, chiral starting materials were usually conducted through this type of reaction. Zhai and co-workers reported the total synthesis of (−)-Jiadifenin, in which the key intermediate was acquired on the basis of Ireland–Claisen rearrangement of chiral acetal precursor 16 . Nakamura developed a stereoselective Ireland–Claisen Rearrangement for the synthesis of the CDE ring system of antitumor and chiral building blocks for oxygenated Terpenoids 17 , 18 .…”

Section: Introductionmentioning

confidence: 99%

Stereodivergent synthesis of vicinal quaternary-quaternary stereocenters and bioactive hyperolactones

Zheng

Wang

et al. 2018

Nat Commun

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Although great success has been achieved in asymmetric Claisen rearrangement for the synthesis of chiral γ,δ-unsaturated carbonyl compounds bearing vicinal tertiary-quaternary stereocenters, the development of asymmetric versions for stereodivergent construction of adjacent quaternary-quaternary stereocenters remains a formidable challenge because of the high steric hindrance. Here we report a catalytic enantioselective dearomatization Claisen rearrangement of allyl furyl ethers catalyzed by chiral N,N′-dioxide-NiII complex catalysts. A variety of chiral γ,δ-unsaturated carbonyl compounds bearing vicinal quaternary-quaternary stereocenters were obtained with excellent outcomes under mild conditions. Furthermore, we disclosed that by matching the configuration of the catalysts and the alkene unit of the substrates, four stereoisomers of the products could be prepared in excellent yields and stereoselectivities. Finally, the fascination of this strategy was demonstrated by stereodivergent synthesis of bioactive natural products hyperolactones B, C, and their epimers. A possible catalytic model was proposed to explain the origin of the asymmetric induction.

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“…[91] Critical to this strategy was an Ireland–Claisen rearrangement [92] to form the C ring of 66 followed by a Pauson–Khand reaction [85] to construct the A ring. Subsequently, an interesting photoinduced [2+2] cycloaddition between a pendant enone and an allene motif was used to install the C9 quaternary center in a diastereoselective manner.…”

Section: Neurotrophic Natural Productsmentioning

confidence: 99%

Neurotrophic Natural Products: Chemistry and Biology

2013

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Neurodegenerative diseases and spinal cord injury affect approximately 50 million people worldwide, bringing the total healthcare cost to over 600 billion dollars per year. Nervous system growth factors, that is, neurotrophins, are a potential solution to these disorders, since they could promote nerve regeneration. An average of 500 publications per year attests to the significance of neurotrophins in biomedical sciences and underlines their potential for therapeutic applications. Nonetheless, the poor pharmacokinetic profile of neurotrophins severely restricts their clinical use. On the other hand, small molecules that modulate neurotrophic activity offer a promising therapeutic approach against neurological disorders. Nature has provided an impressive array of natural products that have potent neurotrophic activities. This Review highlights the current synthetic strategies toward these compounds and summarizes their ability to induce neuronal growth and rehabilitation. It is anticipated that neurotrophic natural products could be used not only as starting points in drug design but also as tools to study the next frontier in biomedical sciences: the brain activity map project.

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Total Synthesis of (−)‐Jiadifenin

Cited by 23 publications

References 51 publications

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Stereodivergent synthesis of vicinal quaternary-quaternary stereocenters and bioactive hyperolactones

Neurotrophic Natural Products: Chemistry and Biology

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Total Synthesis of (−)‐Jiadifenin

Cited by 23 publications

References 51 publications

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Stereodivergent synthesis of vicinal quaternary-quaternary stereocenters and bioactive hyperolactones

Neurotrophic Natural Products: Chemistry and Biology

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Product

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Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions