Abstract:
The reactions of 1,2-unsaturated sugars (glycals) are considered in this review in relation to problems of the enantiospecific synthesis of natural products, their fragments, and their analogues. The reactions occurring both with retention of the heterocycle and those carried out with the aim of obtaining open chain chiral units are discussed. It is shown that the use of glycals as a stock of chiral substances which determine the configuration of the asymmetric centres in the target products of multistage synthesis is promising. Schemes for the synthesis of natural products of different types are considered: O- and C-glycosides, nucleosides, oligosaccharides, pheromones, antibiotics, toxins, glycosphingolipids, etc. The bibliography includes 161 references.
Received: 02.11.1992
Bibliographic databases:
Document Type:
Article
UDC:
542.91+547.455+547.458.2
Language: English
Original paper language: Russian
Citation:
A. G. Tolstikov, G. A. Tolstikov, “Glycals in enantiospecific synthesis”, Usp. Khim., 62:6 (1993), 621–643; Russian Chem. Reviews, 62:6 (1993), 579–601
Linking options:
https://www.mathnet.ru/eng/rcr1109
https://doi.org/10.1070/RC1993v062n06ABEH000034
https://www.mathnet.ru/eng/rcr/v62/i6/p621
This publication is cited in the following 44 articles:
Ornelio Rosati, Massimo Curini, Federica Messina, Maria Carla Marcotullio, Giancarlo Cravotto, Catal Lett, 143:2 (2013), 169
Jianbo Zhang, Bo Zhang, Jiafen Zhou, Heshan Chen, Juan Li, Guofang Yang, Zhongfu Wang, Jie Tang, Journal of Carbohydrate Chemistry, 32:5-6 (2013), 380
Enrique D. V. Giordano, Agustina Frinchaboy, Alejandra G. Suárez, Rolando A. Spanevello, Org. Lett., 14:17 (2012), 4602
Juliano C.R. Freitas, Túlio R. Couto, Antônio A.S. Paulino, João R. de Freitas Filho, Ivani Malvestiti, Roberta A. Oliveira, Paulo H. Menezes, Tetrahedron, 68:51 (2012), 10611
Y. Suman Reddy, Rima Lahiri, Yashwant D. Vankar, Eur J Org Chem, 2012:25 (2012), 4751
Juliano C.R. Freitas, Túlio R. Couto, Antônio A.S. Paulino, João R. de Freitas Filho, Ivani Malvestiti, Roberta A. Oliveira, Paulo H. Menezes, Tetrahedron, 68:41 (2012), 8645
Brijesh Kumar, Mushtaq A. Aga, Abdul Rouf, Bhahwal A. Shah, Subhash C. Taneja, J. Org. Chem., 76:9 (2011), 3506
Laura Alberch, Gang Cheng, Seung-Kee Seo, Xuehua Li, Fabien P. Boulineau, Alexander Wei, J. Org. Chem., 76:8 (2011), 2532