1002-36-4Relevant articles and documents
The first synthesis of tonkinecin, an annonaceous acetogenin with a C-5 carbinol center
Hu, Tai-Shan,Yu, Qian,Lin, Qi,Wu, Yu-Lin,Wu, Yikang
, p. 399 - 401 (1999)
(formula presented) Reported herein is the first synthetic approach to tonkinecin (1) which uses a palladium-catalyzed cross-coupling reaction between the tetrahydrofuran unit (4) and the butenolide (3) as the key step for constructing the backbone of 1. The stereogenic centers at C-5, C-21, C-22, and C-36 were derived from D-xylose, D-glucose, and L-lactate, respectively, whereas those at C-17, and C-18 were generated using Sharpless asymmetric dihydroxylation.
An expeditious synthesis of alk-2-yn-1-ols
Zwierzak, Andrzej,Tomassy, Beata
, p. 3593 - 3600 (1996)
A convenient inexpensive preparation of alk-2-yn-1-ols, commencing from terminal alkynes, has been developed. This procedure allows for using paraformaldehyde instead of gaseous formaldehyde for hydroxymethylation of alk-1-ynylmagnesium bromides.
Synthesis of medium- and large-sized lactones in an aqueous-organic biphasic system
Kinoshita, Hidenori,Shinokubo, Hiroshi,Oshima, Koichiro
, p. 2397 - 2400 (2005)
(Chemical Equation Presented) Saving solvent: An aqueous-ethyl acetate biphasic system allows an efficient synthesis of medium- and large-sized lactones by an intramolecular Tsuji-Trost reaction (see scheme, n = 1-5). The macrocyclization protocol does not require a large quantity of solvents or a slow-addition technique.
A simple, convenient, general procedure for the synthesis of 2-alkyn-1-ylboronates.
Brown, Herbert C.,Roy, Chandra Deo,Soundararajan, Raman
, p. 765 - 768 (1997)
Representative 2-alkyn-1-ylboronates have been synthesized in good to excellent yields using the reaction of the newly available diisopropyl iodomethylboronate with alkynyllithiums generated in situ. Comparable yields are obtained from both acyclic and cyclic boronates. However, 2-(iodomethyl)-1,3,2-dioxa-4,4,5-tetramethylborolane gave superior yields with a wide variety of alkynyllithiums. This procedure offers a simple and convenient alternative route to existing methodologies in terms of the milder reaction condition and the ease of the operation.
Gold(I)-Catalyzed Angle Strain Controlled Strategy to Furopyran Derivatives from Propargyl Vinyl Ethers: Insight into the Regioselectivity of Cycloisomerization
Jin, Shengfei,Jiang, Chongguo,Peng, Xiaoshi,Shan, Chunhui,Cui, Shanshan,Niu, Yuanyuan,Liu, Yang,Lan, Yu,Liu, Yongxiang,Cheng, Maosheng
, p. 680 - 683 (2016)
A unique strategy for the regiospecific synthesis of bicyclic furopyran derivatives has been developed via a gold(I)-catalyzed propargyl-Claisen rearrangement/6-endo-trig cyclization of propargyl vinyl ethers. The introduction of angle strain into the substrates significantly altered the reaction's regioselectivity. Insight into the regioselectivity of the cycloisomerization was obtained with density functional theory calculations. (Chemical Equation).
Preparation and cancer cell invasion inhibitory effects of C16-alkynic fatty acids.
Ohashi, Kazuyoshi,Winarno, Hendig,Mukai, Mutsuko,Shibuya, Hirotaka
, p. 463 - 466 (2003)
Five C(16)-alkynic fatty acids (2-6) were prepared and examined their inhibitory effects on cancer cell invasion. It has been found that hexadeca-6,8,10-triynoic acid (5) and hexadeca-8,10,12-triynoic acid (6) exhibit similar potent inhibitory activities with that of octadeca-8,10,12-triynoic acid (1) which was isolated from Scurrula atropurpurea (Loranthaceae).
Enantioselective Rhodium-Catalyzed Dimerization of ω-Allenyl Carboxylic Acids: Straightforward Synthesis of C2-Symmetric Macrodiolides
Steib, Philip,Breit, Bernhard
, p. 6572 - 6576 (2018)
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.
Facile synthesis of substituted 3-aminofurans through a tandem reaction of N-sulfonyl-1,2,3-triazoles with propargyl alcohols
Cheng, Xing,Yu, Yinghua,Mao, Zhifeng,Chen, Jianxin,Huang, Xueliang
, p. 3878 - 3882 (2016)
A relay catalysis strategy for substituted 3-aminofurans synthesis has been developed. This transformation involves a tandem reaction sequence through aza-vinyl-rhodium(ii) carbene O-H bond insertion, thermal propargyl-Claisen rearrangement and gold(i)-catalyzed intramolecular cyclization. More importantly, the current strategy employs simple feedstocks as starting materials, providing substituted 3-aminofurans in a highly efficient manner.
Synthesis of polyacetylenic acids isolated from Heisteria acuminata
Zeni, Gilson,Panatieri, Rodrigo B.,Lissner, Eliseo,Menezes, Paulo H.,Braga, Antonio L.,Stefani, Helio A.
, p. 819 - 820 (2001)
matrix presented Four linear polyacetylenic compounds were synthesized. Pentadeca-6,8,10-triynoic acid 1 and octadeca-8,10,12-triynoic acid 2 were synthesized by using acetylene coupling reactions. The syntheses of (Z)-hexadec-11-en-7,9-diynoic acid 3 and (Z)-octadec-12-en-7,9-diynoic acid 4 by using vinylic telluride coupling reactions were accomplished.
A Convenient One-Pot Method for the Hydroxymethylation of Grignard Reagents
Ogle, C. A.,Wilson, T. E.,Stowe, J. A.
, p. 495 - 496 (1990)
Grignard reagents and alkynyllithiums can be hydroxymethylated in a two-step one-pot reaction by reaction of a Grignard reagent with 1-chloro-2-(chloromethoxy)ethane (1), followed by treatment with sodium-potassium alloy and aqueous workup.The reaction was found to work for primary, secondary, tertiary, benzylic, allylic and aryl Grignard reagents in yields ranging from 57 - 95 percent.
