53735-49-2Relevant articles and documents
ASYMMETRIC ADDITION OF ACETYLIDE TO ALIPHATIC ALDEHYDES -----PREPARATION OF OPTICALLY ACTIVE 5-OCTYL-2(5H)-FURANONE -----
Mukaiyama, Teruaki,Suzuki, Keisuke
, p. 255 - 256 (1980)
Various optically active acetylenic alcohols (40-80percent e.e.) were obtained by enantioface-differentiating addition of lithium trimethylsilylacetylide to aliphatic aldehydes utilizing (2S, 2'S)-2-hydroxymethyl-1-pyrrolidine as achiral ligand.Optically active (R)-1-trimethylsilyl-1-undecyn-3-ol 80percente.e.) was transformed into optically active 5-octyl-2(5H)-furanone in good yield.
New synthesis of leukotriene B3 methyl ester from bis(trimethylsilyl) unsaturated derivatives
Babudri, Francesco,Fiandanese, Vito,Hassan, Omar,Punzi, Angela,Naso, Francesco
, p. 4327 - 4336 (1998)
A new synthesis of leukotriene B3 methyl ester is reported starting from bis(trimethylsilyl) unsaturated derivatives as building blocks for the triene moiety of the leukotriene. The two stereogenic centers have been generated by enantioselective chemical reduction of two acetylenic ketones with both R- or S-Alpine Borane. The three conjugated double bonds system of the leukotriene has been assembled by Miyaura-Suzuki cross-coupling reaction.
Synthesis of Regioselectively Deuterated Hydroxy Conjugated Dienes
Duffault, Jean-Marc,Einhorn, Jacques,Alexakis, Alexandre
, p. 2765 - 2768 (1995)
A regioselective sythesis of deuterated dienic alcohols has been developed to provide labelled substrates in the frame of gas-phase ion-molecule reaction studies.Key words: regioselective labelling, deuterated dienic alcohol, ion-molecule reaction.
Enantioselective Synthesis and Antifungal Activity of C18 Polyacetylenes
Ding, Shengli,Feng, Jiayang,Li, Changkai,Li, Honglian,Li, Qing X.,Liu, Jia,Lu, Shichao,Na, Risong,Pei, Yiming,Wang, Wenliang,Zhang, Meng
, p. 2116 - 2123 (2020/03/06)
Fungal pathogens cause serious crop diseases and decrease crop yields and quality. Polyacetylene alcohols are plant secondary metabolites and bioactive against various pathogenic fungi. They are, however, difficult to synthesize. In the present study, an efficient and highly enantioselective method (>98% ee) was established and employed to achieve the synthesis of the natural C18 polyacetylenes (S,E)-octadeca-1,9-dien-4,6-diyn-3-ol 1, (3R,10R,E)-octadeca-1,8-dien-4,6-diyne-3,10-diol 2, and their analogs. The title compounds were structurally characterized and biologically evaluated for fungicidal activities. The compounds exhibited high potencies against eight pathogenic fungal species tested, such as Colletotrichum gloeosporioiles, Bipolaris sorokiniana, Fusarium graminearum, and Fusarium pseudograminearum, with half-maximum effective concentrations ranging from 8 to 425 μg/mL, being similar to those of the fungicide thiophanate-methyl (3-408 μg/mL). These compounds are potential natural fungicides and fungicide lead candidates for further structural and property improvements.
Catalytic Nucleophilic Fluorination of Secondary and Tertiary Propargylic Electrophiles with a Copper-N-Heterocyclic Carbene Complex
Cheng, Li-Jie,Cordier, Christopher J.
supporting information, p. 13734 - 13738 (2015/11/11)
A catalytic method for the nucleophilic fluorination of propargylic electrophiles is described. Our protocol involves the use of a Cu(NHC) complex as the catalyst and is suitable for the preparation of secondary and tertiary propargylic fluorides without
Br?nsted acid-catalyzed meyer-schuster rearrangement for the synthesis of α, β -unsaturated carbonyl compounds
Park, Jungmin,Yun, Jihee,Kim, Jaehyun,Jang, Dong-Jin,Park, Cheol Ho,Lee, Kooyeon
supporting information, p. 1924 - 1929 (2014/07/07)
An efficient and simple protocol for the Meyer-Schuster rearrangement of propargyl alcohols into α,β-unsaturated carbonyl compounds has been developed using catalytic amounts of p-toluenesulfonic acid in 1,2-dichloroethane.
Chemoenzymatic total synthesis of paecilocin A and 3-butyl-7- hydroxyphthalide
Sreelakshmi, Ch.,Bhaskar Rao,Lakshmi Narasu,Janardhan Reddy,Reddy, B.V. Subba
, p. 1303 - 1305 (2014/03/21)
A highly enantioselective total synthesis of paecilocin A and 3-butyl-7-hydroxyphthalide is described. The key steps involved in this synthesis are enzymatic kinetic resolution and Alder-Rickert reaction.
Total synthesis of (-)-isoavenaciolide
Santos, David,Ariza, Xavier,Garcia, Jordi,Lloyd-Williams, Paul,Martínez-Laporta, Agustín,Sánchez, Carolina
, p. 1519 - 1524 (2013/03/29)
An enantioselective approach to (-)-isoavenaciolide was achieved starting from 1-undecyn-3-ol. The synthesis relied upon the preparation of a chiral 4-silyloxy-2-alkenylborane by hydroboration of a protected 2,3-allenol and subsequent stereoselective addition to 2-thiophenecarboxaldehyde.
Pheromone synthesis. Part 249: Syntheses of methyl (R,E)-2,4,5- tetradecatrienoate and methyl (2E,4Z)-2,4-decadienoate, the pheromone components of the male dried bean beetle, Acanthoscelides obtectus (Say)
Mori, Kenji
experimental part, p. 1936 - 1946 (2012/04/10)
The enantiomers of methyl (E)-2,4,5-tetradecatrienoate (1), a component of the male pheromone of Acanthoscelides obtectus, were synthesized from the enantiomers of 1-undecyn-3-ol (6), which were obtained via asymmetric acetylation of (±)-1-trimethylsilyl-1-undecyn-3-ol (4) with vinyl acetate as catalyzed by lipase PS (Amano). The ortho ester Claisen rearrangement of 6 with triethyl orthoacetate was the key-step to generate the chiral allenic system. A new synthesis of (±)-1 was also executed starting from (±)-6. Three different syntheses of methyl (2E,4Z)-2,4-decadienoate (2), another component of the male pheromone of A. obtectus, were achieved by means of either palladium-catalyzed Heck reaction or a Claisen and an Al 2O3 catalyzed thermal rearrangements.
An 1,2-Elimination Approach to the Enantioselective Synthesis of 1,3-Disubstituted Linear Allenes
Zhang, Yan,Hao, Hong-Dong,Wu, Yikang
supporting information; experimental part, p. 905 - 908 (2010/08/05)
The construction of 1,3-disubstituted allene skeleton, which is present in many natural allenes, via an i-PrMgBr-mediated elimination of optically active 3-acetoxy-2-iodo-prop-1-ene derviatives is exemplified through the enantioselective total synthesis o
