Institut für Organische Chemie and ‡Institut für Anorganische und Analytische Chemie, Technische Universität Braunschweig , Hagenring 30, 38106 Braunschweig, Germany.
Org Lett. 2017 Apr 7;19(7):1914-1917. doi: 10.1021/acs.orglett.7b00675. Epub 2017 Mar 30.
The enantioselective synthesis of (+)-lysergol was completed in 12 steps and an overall yield of 13% starting from a known literature precursor. The key step relies on a domino reaction containing a formal anti-carbopalladation, which is terminated by a β-silyl-directed Heck reaction. During this transformation, the two six-membered rings of the ergot scaffold are formed in a completely stereospecific manner.
(+)-麦角醇的对映选择性合成以已知文献前体为起始原料,经 12 步反应,总收率为 13%。关键步骤依赖于包含形式反碳钯化的多米诺反应,该反应由β-硅基导向 Heck 反应终止。在这个转变过程中,麦角骨架的两个六元环以完全立体专一的方式形成。