Elucidation of the Sharpless epoxidation of zerumbol

Kitayama, Takashi; Furuya, Atsushi; Moriyama, Chiyuki; Masuda, Tomomi; Fushimi, Sachiko; Yonekura, Yuji; Kubo, Haruko; Kawai, Yasushi; Sawada, Seiji

doi:10.1016/j.tetasy.2006.06.049

Cited by 23 publications

(10 citation statements)

References 12 publications

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“…Zingiber zerumbet (L.) smith or Zingiber aromaticum. It contains three double bonds, two conjugated and one isolated, as well as a conjugated carbonyl group in 11-membrane ring structure [16,17]. Among parts of the plant richest in ZER are rhizomes followed by the leaves [18,19].…”

Section: Zerumbonementioning

confidence: 99%

The Role of Natural Dietary Products in Nanomedicine

Rahman¹,

Othman²,

RasedeeAbdullah³

et al. 2019

Nanomedicines

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It has long been established that a diet rich in fresh fruits, vegetables, seeds, grains and legumes and antioxidants, and other beneficial compounds may help prevent various human diseases. However, diet is not a cure for treatment of severe diseases, but it may help prevent some ailments, and it can help the body overcome the effects of conventional treatments. Natural compounds not only serve as a drug or template for drugs but also, in many instances, had been a source of discovery of novel biology that provided better understanding of target and pathway involved in the disease processes. In addition, drugs derived from natural compounds work better for patients than do drugs manufactured synthetically. Approximately, 40% of drugs in the pipeline and 70% of synthetic therapeutic molecules are plagued with poor solubility, oral bioavailability, and delivery. Drugs with poor solubility encounter limited transport during oral administration because of low concentration gradient between the gut and the blood vessels. To increase body fluid saturation solubility of poorly soluble drug, new delivery methods need to be developed using natural dietary plant metabolites.

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Section: Zerumbonementioning

confidence: 99%

The Role of Natural Dietary Products in Nanomedicine

Rahman¹,

Othman²,

RasedeeAbdullah³

et al. 2019

Nanomedicines

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“…The nucleophilic addition of a second cyanide ion to the carbonyl group opens the strained cyclopropanone to generate another carbanion at C11, which displaces the remaining bromine, creating the final cyclopropane ring (13). Acyl cyanide is rapidly hydrolyzed to yield acids 14a and 14b.…”

Section: Double Favorskii Rearrangementmentioning

confidence: 99%

“…The final yield and ee of (þ)-36 were 38% and 89% respectively. 12,13) Consequently, the Sharpless asymmetric epoxidation (with L-DET) of racemic zerumbol 34 gave racemic 2,3-epoxide 36 regioselectively but not enantioselectively. A second in situ epoxidation step led to efficient kinetic resolution of 36 to afford (À)-35 with 99% ee.…”

Section: Sharpless Epoxidation Of Zerumbolmentioning

confidence: 99%

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Attractive Reactivity of a Natural Product, Zerumbone

Kitayama

2011

Bioscience, Biotechnology, and Biochemistry

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Zerumbone is a cyclic seaquiterpene and, a potential resource for natural materials-related diversityoriented synthesis (NMRDOS). Zerumbone, the main component of the essential oil of a wild ginger, Zingiber zerumbet Smith, showed strong reactivity with good chemo-, regio-, and stereoselectivity. To build the foundations for the industrial use of zerumbone, we examined conjugate addition, transannular reactions, ring cleavage, ring expansion, and asymmetric induction. The biological activity of zerumbone derivatives was also studied.

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“…It is proposed that the reaction ee proceeds with a diastereoselective but non-enantioselective monoepoxidation at the 2,3-position followed by a second highly enantioselective epoxidation at the 10,11de position giving efficient kinetic resolution. 225 The enantioselective oxidation of β-keto sulfides with TBHP in the presence of a titanium complex with (S,S)-hydrobenzoin is a convenient route to the corresponding β-ketosulfoxides in terms of reaction conditions, yields and enantioselectivities (ee > 98%). Aryl ketosulfoxides on reduction ee with DIBAL-ZnCl 2 yielded the corresponding β-sulfinyl alcohols with a retention of configuration.…”

Section: Peracids and Peroxidesmentioning

confidence: 99%

Oxidation and Reduction

Banerji¹

2010

Organic Reaction Mechanisms · 2006

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Elucidation of the Sharpless epoxidation of zerumbol

Cited by 23 publications

References 12 publications

The Role of Natural Dietary Products in Nanomedicine

The Role of Natural Dietary Products in Nanomedicine

Attractive Reactivity of a Natural Product, Zerumbone

Oxidation and Reduction

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