Alkaloids of Picea

Schneider, Marilyn J.; Montali, Julie A.; Hazen, Deborah; Stanton, Colby E.

doi:10.1021/np50075a031

Cited by 44 publications

(17 citation statements)

References 4 publications

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“…here, that since the biological activity usually is highly enantiomer specific, and in coniferous trees, such as Norway spruce, epidihydropinidine appears in the (+)-enantiomeric form [61,62], further antimicrobial studies are needed using pure (+)-epidihydropinidine and (-)-epidihydropinidine. In the racemic mixture of epidihydropinidine, which we have used in this investigation, the activity could be ACCEPTED MANUSCRIPT…”

Section: Discussionmentioning

confidence: 99%

“…Norway spruce needles and young stems contain a number of small molecular mass piperidine alkaloids, epidihydropinidine and cis-pinidinol being the most abundant ones [55,56,61]. Piperidine alkaloids in conifers are thought to be insect antifeedants but have also been reported to be toxic and teratogenic in a frog embryo test [61,62,63]. Less is known about their possible role as antifungals and antibacterials.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

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Epidihydropinidine, the main piperidine alkaloid compound of Norway spruce (Picea abies) shows promising antibacterial and anti-Candida activity

et al. 2017

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ArtikkelitLuonnontieteiden This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. A C C E P T E D M A N U S C R I P T

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Section: Discussionmentioning

confidence: 99%

Section: Accepted Manuscriptmentioning

confidence: 99%

Epidihydropinidine, the main piperidine alkaloid compound of Norway spruce (Picea abies) shows promising antibacterial and anti-Candida activity

et al. 2017

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“…It has been found to have antifeedant activity against spruce budworm. 44 Pinidinol has been synthesized [45][46][47] using asymmetric hydroamination/ cyclization as the key step. 48 The enantiomerically pure substrate 23 upon hydroamination/cyclization in the presence of Cp Ã 2 NdCH(TMS) 2 24 results in the formation of piperidine 25 as a single diastereomer in 89% yield.…”

Section: Asymmetric and Diastereoselective Hydroamination In Total Symentioning

confidence: 99%

Asymmetric Hydroamination and Reductive Amination in Total Synthesis

Ghorai

Tiwari

Bhattacharyya

2013

Stereoselective Synthesis of Drugs and Natural Products

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Asymmetric hydroamination (AHA) and asymmetric reductive amination (ARA) are one of the most popular strategies for enantioselective synthesis of chiral amines, which are very important from a synthetic and a biological point of view. The addition of the NH bond across an unsaturated CC bond is known as hydroamination. AHA is ideal for industrial processes as it is a 100% atom‐economic reaction and involves readily available substrates. For broadening its scope for a variety of substrates, many metal‐based as well as metal‐free catalytic systems have been developed for asymmetric hydroamination. Along with the synthesis of functionalized chiral amines, AHA has served as a key strategy in the synthesis of the core of various natural products like codeine, pseudodistomin, swainsonine and of drugs like pentazocine. Reductive amination is a widely used efficient synthetic protocol to install an amine group in place of a carbonyl group in an organic compound. The reaction proceeds through the formation of imine and subsequent one‐pot reduction of it to give the product amine. Use of a metal‐chiral ligand combination, chiral Brønsted acid or chiral organocatalyst, or chiral auxiliary in the reaction can give rise to chiral amine products that are often valuable synthetic intermediates en route to many drugs and natural products. Application of these protocols in the total synthesis of drugs and natural products will be discussed along with some experimental procedures.

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“…NMR C (CDCl 3 ): 14. 3,18.5,24.4,24.8,34.1,35.5,36.6,37.9,55.5,66.2,77.1,77.2,95.4,127.3,128.9,129.4,135.3,153.4,173.2. Anal.…”

Section: (4s)-4-benzyl-3-[(s)-6-methoxymethoxynonanoyl]-2-oxazolidinomentioning

confidence: 99%

“…Anal. Found: C,66.75;H,8.19;N,3. (4S)-4-Benzyl-3-[(2S,6S)-2-hydroxy-6-methoxymethoxynonanoyl]-2-oxazolidinone (19). To a solution of (4S)-[(S)]-18 (10.7 g, 0.028 mol) in THF (300 ml) was added KHMDS (84.9 ml, 0.5 M in toluene, 0.042 mol) at À70 C. After stirring at À70 C for 30 min, MoOPH (18.5 g, 0.043 mol) was added.…”

Section: (4s)-4-benzyl-3-[(s)-6-methoxymethoxynonanoyl]-2-oxazolidinomentioning

confidence: 99%

Syntheses of (+)- and (−)-Dihydropinidine and (+)- and (−)-Epidihydropinidine by Using Yeast Reduction of Methyl (2-oxocyclohexyl)acetate

Yamauchi

Mori

Hirai

et al. 2004

Bioscience, Biotechnology, and Biochemistry

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Alkaloids of Picea

Cited by 44 publications

References 4 publications

Epidihydropinidine, the main piperidine alkaloid compound of Norway spruce (Picea abies) shows promising antibacterial and anti-Candida activity

Epidihydropinidine, the main piperidine alkaloid compound of Norway spruce (Picea abies) shows promising antibacterial and anti-Candida activity

Asymmetric Hydroamination and Reductive Amination in Total Synthesis

Syntheses of (+)- and (−)-Dihydropinidine and (+)- and (−)-Epidihydropinidine by Using Yeast Reduction of Methyl (2-oxocyclohexyl)acetate

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