An Oxidative Prins-Pinacol Tandem Process and its Application to the synthesis of (-)-Platensimycin

被引：66
作者：
Beaulieu, Marc-Andre [1 ]
Sabot, Cyrille [1 ]
Achache, Nabil [1 ]
Guerard, Kimiaka C. [1 ]
Canesi, Sylvain [1 ]
机构：
[1] Univ Quebec, Dept Chim, Lab Methodol & Synth Prod Nat, Montreal, PQ H3C 3P8, Canada
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 37期
基金：
加拿大创新基金会; 加拿大自然科学与工程研究理事会;
关键词：
hypervalent compounds; iodine; natural products; oxidation; Prins-pinacol reaction; umpolung; HYPERVALENT IODINE(III) REAGENT; FORMAL 2+3 CYCLOADDITION; CARBON BOND FORMATION; HYDROXYLATIVE PHENOL DEAROMATIZATION; ENANTIOSELECTIVE TOTAL-SYNTHESIS; ALPHA-ALKOXY HYDROPEROXIDES; (+/-)-SCOPADULCIC ACID-A; BIARYL COUPLING REACTION; AROMATIC RING UMPOLUNG; 1ST TOTAL-SYNTHESIS;
D O I：
10.1002/chem.201001813
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Center stage: An oxidative Prins-pinacol tandem process mediated by a hypervalent iodine reagent has been accomplished. The strategy allows rapid access to highly functionalized spirocyclic cores (see scheme) present in many natural products. A first application to the formal synthesis of (?)-platensimycin has been achieved. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：11224 / 11228
页数：5
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