手性催化的四氢异喹啉及其含 C4 立体中心类似物的对映选择性合成：(+)-(8S,13R)-环科拉宾碱的形式合成。
Catalytic enantioselective synthesis of tetrahydroisoquinolines and their analogues bearing a C4 stereocenter: formal synthesis of (+)-(8S,13R)-cyclocelabenzine.
机构信息
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, China.
出版信息
Chemistry. 2013 Jun 24;19(26):8426-30. doi: 10.1002/chem.201301065. Epub 2013 May 15.
PMID:23677731
Abstract
A one-pot wonder: 1,2,3,4-Tetrahydroisoquinolines with a C4 stereocenter can be formed by using a one-pot multicomponent chiral phosphoric acid catalyzed transformation of a mixture of oxetane-tethered benzaldehydes, amines, and the dimethyl ester derivative of the Hantzsch ester (see scheme). This transformation can be used to prepare the spermidine alkaloid (+)-(8S,13R)-cyclocelabenzine.
摘要
一锅法的奇迹
通过一锅多组分手性磷酸催化的混合氧杂环丁烷缩醛-苯甲醛、胺和 Hantzsch 酯的二甲酯衍生物的转化，可以形成具有 C4 立体中心的 1,2,3,4-四氢异喹啉（见方案）。这种转化可用于制备 spermidine 生物碱（+）-（8S,13R）-cyclocelabenzine。
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