Krishnan Shyam, Bagdanoff Jeffrey T, Ebner David C, Ramtohul Yeeman K, Tambar Uttam K, Stoltz Brian M
The Arnold and Mabel Beckman Laboratories of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Boulevard, MC 164-30, Pasadena, California 91125, USA.
J Am Chem Soc. 2008 Oct 15;130(41):13745-54. doi: 10.1021/ja804738b. Epub 2008 Sep 18.
Enantioselective syntheses of the alkaloids (-)-aurantioclavine, (+)-amurensinine, (-)-lobeline, and (-)- and (+)-sedamine are described. The syntheses demonstrate the effectiveness of the Pd-catalyzed asymmetric oxidation of secondary alcohols in diverse contexts and the ability of this methodology to set the absolute configuration of multiple stereocenters in a single operation. The utility of an aryne C-C insertion reaction in accessing complex polycyclic frameworks is also described.
描述了生物碱（-）-橙黄麦角碱、（+）-紫堇灵、（-）-洛贝林以及（-）-和（+）-水苏碱的对映选择性合成。这些合成展示了钯催化仲醇不对称氧化在不同背景下的有效性，以及该方法在单一操作中确定多个立体中心绝对构型的能力。还描述了芳炔C-C插入反应在构建复杂多环骨架中的应用。
