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Radical Cyclization/ipso‐1,4‐Aryl Migration Cascade: Asymmetric Synthesis of 3,3‐Difluoro‐2‐propanoylbicyclo[3.3.0]octanes 下载免费PDF全文
Watcharaporn Thaharn Dr. Darunee Soorukram Dr. Chutima Kuhakarn Dr. Patoomratana Tuchinda Prof. Dr. Vichai Reutrakul Prof. Dr. Manat Pohmakotr 《Angewandte Chemie (International ed. in English)》2014,53(8):2212-2215
A novel method for the asymmetric synthesis of 3,3‐difluoro‐2‐propanoylbicyclo‐[3.3.0]octanes involves an unprecedented intramolecular radical cyclization/ipso‐1,4‐aryl migration cascade. 相似文献
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Punirun T Peewasan K Kuhakarn C Soorukram D Tuchinda P Reutrakul V Kongsaeree P Prabpai S Pohmakotr M 《Organic letters》2012,14(7):1820-1823
Fluoride-catalyzed stereoselective nucleophilic addition of PhSCF(2)SiMe(3) (1) to α-carboethoxycycloalkanones 2 followed by intramolecular radical cyclization of the resulting cis-3 adduct afforded the corresponding gem-difluoromethylenated bicyclic compounds 4, which underwent ring-expansion followed by the Baeyer-Villiger-type oxidation of the resulting macrocyclic ketone intermediates to give gem-difluoromethylenated macrocyclic lactones 5. 相似文献
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Chonticha Masusai Darunee Soorukram Chutima Kuhakarn Patoomratana Tuchinda Chaveng Pakawatchai Vichai Reutrakul Manat Pohmakotr 《Helvetica chimica acta》2012,95(10):1912-1927
The Morita? Baylis? Hillman (MBH) reactions of (4S,5R,7R,8R)‐ and (4R,5R,7R,8R)‐4‐hydroxy‐7,8‐dimethoxy‐7,8‐dimethyl‐6,9‐dioxaspiro[4.5]dec‐2‐en‐1‐ones ( 2 and 3 , resp.) with aldehydes using various catalysts were studied. A combination of Bu3P/phenol in THF was found being optimum conditions giving the corresponding MBH adducts with high diastereoisomeric ratios. After separation, each stereomerically pure isomer of the MBH adducts was subjected to hydrolysis employing 1% aq. CF3COOH (TFA) in a water bath of an ultrasonic cleaner to afford the corresponding polyhydroxylated cyclopentenones in good yields. 相似文献
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Pramchai Deelertpaiboon Suwatchai Jarussophon Patoomratana Tuchinda Chutima Kuhakarn Manat Pohmakotr 《Tetrahedron letters》2009,50(46):6233-6235
Treatment of glycals with trialkylaluminum in the presence of a catalytic amount of Yb(OTf)3 leads to the corresponding alkyl 2,3-unsaturated glycosides in good to excellent yields. Reactions of protected glycals are achieved under very mild conditions. 相似文献
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An efficient route to the -protected spirenones (2c) and (2d) is described: from these, the five known natural spirans of cannabis, i.e. cannabispiradienone (1a), cannabispirenone-A (2a), cannabispirenone-B (2b), cannabispirone (3a) and cannabispiranol (4a), are synthesised. 相似文献
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Chooprayoon S Kuhakarn C Tuchinda P Reutrakul V Pohmakotr M 《Organic & biomolecular chemistry》2011,9(2):531-537
A concise asymmetric synthesis of (+)-swainsonine (ent-1) is described starting from 2, which was readily prepared from commercially available l-glutamic acid. The method features installation of the indolizidine ring via an intramolecular cyclisation of α-sulfinyl carbanion as a key step. (+)-Swainsonine was obtained in 11.8% overall yield in 10 steps. 相似文献
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Manat Pohmakotr Darunee Soorukram Patoomratana Tuchinda Samran Prabpai Palangpon Kongsaeree Vichai Reutrakul 《Tetrahedron letters》2004,45(22):4315-4318
The vicinal dianions derived from chiral succinic acid derivatives, 1,4-bis[(4R,5S)-3,4-dimethyl-2-oxo-5-phenylimidazolidin-1-yl]butane-1,4-dione and 1,4-bis[(4S,5R)-3,4-dimethyl-2-oxo-5-phenylimidazolidin-1-yl]butane-1,4-dione react with arylmethyl bromides with high diastereo- and regio-selectivity to provide the corresponding chiral α-arylmethylated succinic acid derivatives; the (R)-products are converted into (R)-β-arylmethyl-γ-butyrolactones and (R)-α-arylmethyl-γ-butyrolactones. 相似文献
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Pohmakotr M Yotapan N Tuchinda P Kuhakarn C Reutrakul V 《The Journal of organic chemistry》2007,72(13):5016-5019
Functionalized gamma-lactams are found to be crucial intermediates in the synthesis of biologically important natural products. We herein described a highly diastereoselective synthesis of beta-carboxy-gamma-lactams and their ethyl ester derivatives, in high yields with high diastereomeric ratio, via the Mukaiyama-aldol type reaction of 2,5-bis(trimethysilyloxy)furan with imines, employing Sc(OTf)(3) as a catalyst. 相似文献
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Darunee Soorukram Jaray PanmuangPatoomratana Tuchinda Chutima KuhakarnVichai Reutrakul Manat Pohmakotr 《Tetrahedron》2014
A stereoselective approach to secolignans is described. The key synthetic strategy involves an asymmetric aldol reaction to control the creation of the stereogenic center at the β-carbon of the target secolignans. In the present work, peperomin C and its analogues, i.e., 2,6-didehydropeperomin C and 2-epi-peperomin C were successfully synthesized in good yields with high stereoselectivities. 相似文献