Total synthesis of each enantiomer of falcarinol and panaxjapyne A via asymmetric catalytic alkynylation of an aldehyde

Yang, Yanqing; Li, Shuoning; Zhong, Jiangchun; Zhou, Yun; Zeng, Hao‐Zhe; Duan, H.-F.; Bian, Qinghua; Wang, Min

doi:10.1016/j.tetasy.2015.02.010

Cited by 17 publications

(10 citation statements)

References 34 publications

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“…: comparison with literature data. All compounds were identified by comparing their EI‐MS and retention indices with references compiled in the in‐house library, except falcarinol ( 23 ), dodecanoic acid ( 21 ), 3,4‐dimethyl‐5‐pentyl‐5 H ‐furan‐2‐one ( 19 ), and 3‐undecen‐1‐yne ( 12 ), identified from MS literature data …”

Section: Resultsmentioning

confidence: 99%

“…It has also a protective effect on the Amyloid β protein, the central constituent of senile plaques in Alzheimer 's disease . As falcarinol have been produced by multi‐steps enantioselective synthesis, identifying possible valuable natural sources of this phytochemical from plant essential oils presents an interesting challenge. In the Eryngium genus, only once has falcarinol been identified as the main component, in E .…”

Section: Introductionmentioning

confidence: 99%

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Chemical Composition and Biological Investigations of Eryngium triquetrum Essential Oil from Algeria

Medbouhi

Merad

Khadir

et al. 2017

Chemistry & Biodiversity

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The chemical composition, antibacterial and antioxidant activities of the essential oil obtained from Eryngium triquetrum from Algeria were studied. The chemical composition of sample oils from 25 locations was investigated using GC-FID and GC/MS. Twenty-four components representing always more than 87% were identified in essential oils from total aerial parts of plants, stems, flowers and roots. Falcarinol is highly dominant in the essential oil from the roots (95.5%). The relative abundance of falcarinol in the aerial parts correlates with the phenological stages of the plant. Aerial parts of E. triquetrum produce an essential oil dominated by falcarinol during the early flowering stage, and then there is a decrease in falcarinol and rebalancing of octanal during the flowering stage. To our knowledge, the present study is the first report of the chemical composition of E. triquetrum essential oil. Evaluation of the antibacterial activity by means of the paper disc diffusion method and minimum inhibitory concentration assays, showed a moderate efficiency of E. triquetrum essential oil. Using the DPPH method, the interesting antioxidant activity of E. triquetrum essential oil was established. These activities could be attributed to the dominance of falcarinol. The outcome of our literature search on the occurrence of falcarinol in essential oils suggests that E. triquetrum from Algeria could be considered as a possible source of natural falcarinol.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Chemical Composition and Biological Investigations of Eryngium triquetrum Essential Oil from Algeria

Medbouhi

Merad

Khadir

et al. 2017

Chemistry & Biodiversity

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“…The BINOL-ZnEt 2 -Ti (IV) complex catalyzed asymmetric addition of trimethylsilylacetylene to the aliphatic aldehydes was well developed by Pu’s group [ 20 , 22 , 34 ]. It is also a practical approach for providing chiral acetylene alcohols.…”

Section: Resultsmentioning

confidence: 99%

“…Highly enantioselective methyl propiolate ( S )- 13 is obtained by Zn-catalyzed asymmetric addition of terminal alkynes 15 to various aldehydes 14 . This reaction has been widely studied ( Scheme 2 ) [ 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 ], in which numerous chiral ligands are applied, such as ( R , R )-ProPhenol 16 a [ 24 , 39 ], ( R )-BINOL 17 a , and its derivatives [ 28 , 30 ], β-Sulfonamide Alcohol 18 [ 31 , 32 ], Wolf’s ligand 19 [ 41 ], and Wang’s ligand 20 (our previous group research) [ 33 ]. Among the numerous catalysts, ( R , R )-ProPhenol 16 a and ( R )-BINOL 17 a are readily available and well-established [ 20 , 21 , 22 , 23 , 24 , …”

Section: Introductionmentioning

confidence: 99%

A General Asymmetric Synthesis of (R)-Matsutakeol and Flavored Analogs

Jia

Zheng

et al. 2017

Molecules

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An efficient and practical synthetic route toward chiral matsutakeol and analogs was developed by asymmetric addition of terminal alkyne to aldehydes. (R)-matsutakeol and other flavored substances were feasibly synthesized from various alkylaldehydes in high yield (up to 49.5%, in three steps) and excellent enantiomeric excess (up to >99%). The protocols may serve as an alternative asymmetric synthetic method for active small-molecule library of natural fatty acid metabolites and analogs. These chiral allyl alcohols are prepared for food analysis and screening insect attractants.

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“…A few groups have devoted their work in this aspect and have made impressive progress, though there are still limitations in their methods [13][14][15]. Yang et al have synthesized the falcarinol and panaxjapyne A by the asymmetric addition of alkynylzinc reagents to acrolein and propionaldehyde catalyzed by a 1,1'-bi-2-naphthol (BINOL)/Ti(O i Pr)4 complex and a classic Cadiot-Chodkiewicz cross-coupling reaction with high enantioselectivity (>99% ee) [16]. Zheng et al have successfully synthesized (S)-strongylodiol A and (S)-strongylodiol B, which were extracted from an Okinawan marine sponge of the genus Strongylophora and exhibited cytotoxic activities against tumor cells, by using a zinc-amino alcohol complex catalyzed 1,3-diynes addition to aldehydes with respective ee values of 55% and 58% [17,18].…”

Section: Resultsmentioning

confidence: 99%

Total Synthesis of Chiral Falcarindiol Analogues Using BINOL-Promoted Alkyne Addition to Aldehydes

et al. 2016

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An enantioselective total synthesis of chiral falcarindiol analogues from buta-1,3-diyn-1-yltriisopropylsilane is reported. The key step in this synthesis is BINOL-promoted asymmetric diacetylene addition to aldehydes. The two chiral centers of the falcarindiol analogues can be produced by using the same kind of catalyst with high selectivity, and the final product can be obtained in only six steps.

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Total synthesis of each enantiomer of falcarinol and panaxjapyne A via asymmetric catalytic alkynylation of an aldehyde

Cited by 17 publications

References 34 publications

Chemical Composition and Biological Investigations of Eryngium triquetrum Essential Oil from Algeria

Chemical Composition and Biological Investigations of Eryngium triquetrum Essential Oil from Algeria

A General Asymmetric Synthesis of (R)-Matsutakeol and Flavored Analogs

Total Synthesis of Chiral Falcarindiol Analogues Using BINOL-Promoted Alkyne Addition to Aldehydes

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