figshare
Browse
ol7b00675_si_001.pdf (1.71 MB)

Enantioselective Total Synthesis of (+)-Lysergol: A Formal anti‑Carbopalladation/Heck Cascade as the Key Step

Download (1.71 MB)
journal contribution
posted on 2017-03-29, 21:19 authored by Bastian Milde, Martin Pawliczek, Peter G. Jones, Daniel B. Werz
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.

History