Asymmetric Synthesis of α-Alkylidene-β-hydroxy-γ-butyrolactones via Enantioselective Tandem Michael–Aldol Reaction
作者： Sung Il Lee , Jin Hee Jang , Geum-Sook Hwang , Do Hyun Ryu
DOI: 10.1021/JO302369Q
关键词:
摘要: A simple and efficient method for the asymmetric synthesis of α-alkylidene-β-hydroxy-γ-butyrolactones related natural products was developed on basis catalytic tandem Michael–aldol reaction transformations. The synthetic utility this illustrated by facile trisubstituted γ-butyrolactone products.
acs.org
sci-hub.se 参考文章(34)
Ken'ichi Takeda, K. Sakurawi, H. Ishii, Components of the Lauraceae family—I Tetrahedron. ,vol. 28, pp. 3757- 3766 ,(1972) , 10.1016/S0040-4020(01)93822-0
Ian-Lih Tsai, Chao-Hui Hung, Chang-Yih Duh, Jyh-Huey Chen, Wei-Yu Lin, Ih-Sheng Chen, Cytotoxic Butanolides from the Stem Bark of Formosan Lindera communis Planta Medica. ,vol. 67, pp. 865- 867 ,(2001) , 10.1055/S-2001-18840
Ih-Sheng Chen, I-Lun Lai-Yaun, Chang-Yih Duh, Ian-Lih Tsai, Cytotoxic butanolides from Litsea akoensis Phytochemistry. ,vol. 49, pp. 745- 750 ,(1998) , 10.1016/S0031-9422(98)00129-0
Do Hyun Ryu, Lizhu Gao, Geum-Sook Hwang, Oxazaborolidinium ion-catalyzed cyclopropanation of α-substituted acroleins: enantioselective synthesis of cyclopropanes bearing two chiral quaternary centers. Journal of the American Chemical Society. ,vol. 133, pp. 20708- 20711 ,(2011) , 10.1021/JACS.1C03211
Su-Yen Chang, Ming-Jen Cheng, Chien-Fang Peng, Hsun-Shuo Chang, Ih-Sheng Chen, Antimycobacterial Butanolides from the Root of Lindera akoensis Chemistry & Biodiversity. ,vol. 5, pp. 2690- 2698 ,(2008) , 10.1002/CBDV.200890223
Renan S. Ferrarini, Alcindo A. Dos Santos, João V. Comasseto, Tellurium in organic synthesis: a new approach to trisubstituted γ-butyrolactones with trans–trans relative stereochemistry. Total enantioselective synthesis of (−)-Blastmycinolactol, (+)-Blastmycinone, (−)-NFX-2, and (+)-Antimycinone Tetrahedron Letters. ,vol. 51, pp. 6843- 6846 ,(2010) , 10.1016/J.TETLET.2010.10.089
Jean-Pierre Lepoittevin, Valérie Berl, Elena Giménez-Arnau, α-methylene-γ-butyrolactones: versatile skin bioactive natural products† Chemical Record. ,vol. 9, pp. 258- 270 ,(2009) , 10.1002/TCR.200900013
Tadashi Nakata, Tadasu Tanaka, Takeshi Oishi, Stereoselective reduction of α-hydroxy ketones Tetrahedron Letters. ,vol. 24, pp. 2653- 2656 ,(1983) , 10.1016/S0040-4039(00)87969-1
Juan C.V. Martinez, Massayoshi Yoshida, Otto R. Gottlieb, Six groups of ω-ethyl-, ω-ethenyl- and ω-ethynyl-α-alkylidene-γ-lactones Tetrahedron Letters. ,vol. 20, pp. 1021- 1024 ,(1979) , 10.1016/S0040-4039(01)87179-3
Guey-Horng Wang, Chang-Feng Dai, Yao-Haur Kuo, Jyh-Horng Sheu, Atallah F Ahmed, Ru-Ting Shiue, Five novel norcembranoids from Sinularia leptoclados and S. parva Tetrahedron. ,vol. 59, pp. 7337- 7344 ,(2003) , 10.1016/S0040-4020(03)01138-4