Total Synthesis of the Amaryllidaceae Alkaloid (+)-Plicamine and Its Unnatural Enantiomer by Using Solid-Supported Reagents and Scavengers in a Multistep Sequence of Reactions We gratefully acknowledge financial support from Pfizer Central Research for a Postdoctoral Fellowship (to I.R.B.), the BP endowment and the Novartis Research Fellowship (to S.V.L.), and Pharmacia & Upjohn (to C.P.).
作者： Ian R. Baxendale , Steven V. Ley , Claudia Piutti
DOI: 10.1002/1521-3773(20020617)41:12<2194::AID-ANIE2194>3.0.CO;2-4
关键词: Sequence (medicine) 、 Enantiomer 、 Total synthesis 、 Amaryllidaceae 、 Organic chemistry 、 Reagent 、 Chemistry 、 Alkaloid 、 Stereochemistry 、 General chemistry 、 Catalysis
摘要:
sci-hub.se 参考文章(41)
Stephen F. Martin, Chapter 3 The Amaryllidaceae Alkaloids The Alkaloids: Chemistry and Pharmacology. ,vol. 30, pp. 251- 376 ,(1987) , 10.1016/S0099-9598(08)60208-4
Amrik Chawla, T. Krishnan, Anthony Jackson, David Scalabrin, Alkaloidal constituents of Erythrina variegata bark. Planta Medica. ,vol. 54, pp. 526- 528 ,(1988) , 10.1055/S-2006-962538
Y. Tsuda, A. Ukai, K. Isobe, Total syntheses of the alkaloids haemanthidine and tazettine Tetrahedron Letters. ,vol. 13, pp. 3153- 3156 ,(1972) , 10.1016/S0040-4039(01)93990-5
Esameldin E Elgorashi, Siegfried.E Drewes, Johannes Van Staden, Alkaloids from Crinum bulbispermum Phytochemistry. ,vol. 52, pp. 533- 536 ,(1999) , 10.1016/S0031-9422(99)00255-1
James B. Hendrickson, Terry L. Bogard, Marcia E. Fisch, Stuart Grossert, Norman Yoshimura, Stereospecific total synthesis of hemanthidine and tazettine Journal of the American Chemical Society. ,vol. 96, pp. 7781- 7789 ,(1974) , 10.1021/JA00832A027
Marina Caldarelli, Jörg Habermann, Steven V. Ley, Clean five-step synthesis of an array of 1,2,3,4-tetra-substituted pyrroles using polymer-supported reagents Journal of The Chemical Society-perkin Transactions 1. pp. 107- 110 ,(1999) , 10.1039/A809345H
C.W Fennell, J van Staden, Crinum species in traditional and modern medicine. Journal of Ethnopharmacology. ,vol. 78, pp. 15- 26 ,(2001) , 10.1016/S0378-8741(01)00305-1
Steven V. Ley, Olivier Schucht, Andrew W. Thomas, P. John Murray, Synthesis of the alkaloids (±)-oxomaritidine and (±)-epimaritidine using an orchestrated multi-step sequence of polymer supported reagents Journal of The Chemical Society-perkin Transactions 1. pp. 1251- 1252 ,(1999) , 10.1039/A901798D
Jörg Habermann, Steven V. Ley, Jan J. Scicinski, James S. Scott, René Smits, Andrew W. Thomas, Clean synthesis of α-bromo ketones and their utilisation in the synthesis of 2-alkoxy-2,3-dihydro-2-aryl-1,4-benzodioxanes, 2-amino-4-aryl-1,3-thiazoles and piperidino-2-amino-1,3-thiazoles using polymer-supported reagents Journal of The Chemical Society-perkin Transactions 1. pp. 2425- 2427 ,(1999) , 10.1039/A905616E
Ian R Baxendale, Steven V Ley, Polymer-supported reagents for multi-step organic synthesis: application to the synthesis of sildenafil. Bioorganic & Medicinal Chemistry Letters. ,vol. 10, pp. 1983- 1986 ,(2000) , 10.1016/S0960-894X(00)00383-8