4117-14-0Relevant articles and documents
Enantioselective Rhodium-Catalyzed Dimerization of ω-Allenyl Carboxylic Acids: Straightforward Synthesis of C2-Symmetric Macrodiolides
Steib, Philip,Breit, Bernhard
supporting information, p. 6572 - 6576 (2018/05/08)
Herein, we report on the first enantioselective and atom-efficient catalytic one-step dimerization method to selectively transform ω-allenyl carboxylic acids into C2-symmetric 14- to 28-membered bismacrolactones (macrodiolides). This convenient asymmetric access serves as an attractive route towards multiple naturally occuring homodimeric macrocyclic scaffolds and demonstrates excellent efficiency to construct the complex, symmetric core structures. By utilizing a rhodium catalyst with a modified chiral cyclopentylidene-diop ligand, the desired diolides were obtained in good to high yields, high diastereoselectivity, and excellent enantioselectivity.
Total syntheses of 9-epoxyfalcarindiol and its diastereomer
Zhou, Yun,Huang, Yanli,Li, Shuoning,Yang, Pengfei,Zhong, Jiangchun,Yin, Jingwei,Ji, Kaijie,Yang, Yanqing,Ye, Ning,Wang, Lifeng,Wang, Mingan,Wang, Min,Bian, Qinghua
, p. 288 - 295 (2017/02/18)
The first total syntheses of 9-epoxyfalcarindiol 1a and its diastereomer 1b have been achieved. Central to our approach were the Zn-cyclopropane-based amino alcohol catalyzed enantioselective alkynylation of acrolein, the diastereoselective addition of a diynic ester to an epoxy aldehyde, and the asymmetric Sharpless epoxidation of allylic alcohol catalyzed with L-(+)-diethyl tartrate and Ti(OiPr)4.
Total synthesis of panaxydol and its stereoisomers as potential anticancer agents
Mao, Jianyou,Li, Shuoning,Zhong, Jiangchun,Wang, Bo,Jin, Jing,Gao, Zidong,Yang, Hanze,Bian, Qinghua
, p. 69 - 77 (2015/12/31)
An efficient total synthesis of natural panaxydol 1a and its seven stereoisomers 1b-h was accomplished; four diastereomers of the natural form were prepared for the first time. Our strategy involves the Cadiot-Chodkiewicz cross-coupling reaction of chiral terminal alkynes with bromoalkynes, the asymmetric alkynylation of aldehydes, and the enantioselective Sharpless epoxidation of allylic alcohols. Preliminary in vitro cytotoxicity evaluation indicated that some synthetic panaxydols possess anticancer activities, and (3S,9R,10S)-panaxydol 1e showed a particularly promising cytotoxic effect.
Tetris in monolayers: Patterned self-assembly using side chain shape
Xue, Yi,Zimmt, Matthew B.
supporting information; experimental part, p. 8832 - 8834 (2011/09/16)
The "kinked" shapes of conjugated alkadiynes constrain chain packing in monolayers on HOPG. Centrally located diyne units permit assembly of 1,5-bis(alkadiyne)anthracene monolayers. Off-center diynes inhibit self-assembly. Shape matched pairs of off-center diyne chains direct self-assembly of compositionally patterned, two component monolayers.
A short synthesis of (+) and (-)-falcarinol
McLaughlin, Noel P.,Butler, Eibhlín,Evans, Paul,Brunton, Nigel P.,Koidis, Anastasios,Rai, Dilip K.
experimental part, p. 9681 - 9687 (2011/02/25)
A short, practical synthesis of the bis-acetylenic natural product falcarinol 1 is reported. This method relies on the alternate functionalisation of bis-trimethylsilylbutadiyne 10. This may be achieved in one-pot, however, better yields were obtained more conventionally. Lipase mediated enzymatic kinetic resolution of the racemic adduct in an organic solvent afforded (+)-1 in 97% enantiomeric excess. The analogous process performed with racemic 3-acetoxy falcarinol 11 under aqueous conditions gave (-)-1. Oxidation of 1 with Dess-Martin periodinane gave falcarinone 2.
First total synthesis of cyrmenin
Chakor, Narayan S.,Musso, Loana,Dallavalle, Sabrina
scheme or table, p. 844 - 849 (2009/06/20)
A short and efficient synthesis of cyrmenin B1 an antifungal metabolite of myxobacteria Cystobacter armeniaca and Archangium gephyra, is described. The crucial steps of the synthesis included the formation of the dehydroalanine moiety from the corresponding serine acetate and the formation of the β-methoxyacrylate system via trimethylsilyldiazomethane methylation of the corresponding β-hydroxy enamide.
Stereoselective approaches for the total synthesis of polyacetylenic (3R,8S)-falcarindiol
Sabitha, Gowravaram,Bhaskar, Vangala,Reddy, Ch. Srinivas,Yadav, Jhillu S.
, p. 115 - 121 (2008/09/20)
The total synthesis of the polyacetylenic compound falcarindiol was achieved by two different routes from a common intermediate. Georg Thieme Verlag Stuttgart.
Titanocene-catalyzed regiodivergent epoxide openings
Gansaeuer, Andreas,Fan, Chun-An,Keller, Florian,Keil, Jutta
, p. 3484 - 3485 (2008/01/01)
The first regiodivergent opening of unbiased epoxides providing the ring-opened products in high enantiomeric excess from racemic and exceptionally high enantiomeric excess from enantioenriched substrates in a double asymmetric process has been devised. It constitutes a more general case of the very important enantioselective openings of meso-epoxides. Copyright
Synthesis of polyacetylenic acids isolated from Nanodea muscosa
Alves, Diego,Nogueira, Cristina W.,Zeni, Gilson
, p. 8761 - 8764 (2007/10/03)
The first total synthesis of two linear polyacetylenic compounds is described. The synthesis of (E)-octadec-13-en-11-ynoic acid 1 and (E)-octadec-13-en-9,11-diynoic acid 2 by using the vinylic telluride coupling reaction was accomplished.
2-HEPTYLCYCLOPROPYL-1-CARBOXYLIC ACID
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Page/Page column 17, (2010/02/07)
The invention relates to optionally isolated and/or purified enantiomers of 2-heptylcyclopropyl-1-carboxylic acid, in addition to mixtures of two, three or all enantiomers of 2-heptylcyclopropyl-1-carboxylic acid, which are used as perfumes and/or aromatic substances.
