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

Werz, Daniel B.

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

Version 2 2017-03-30, 12:05

Version 1 2017-03-29, 21:19

Posted on 2017-03-30 - 12:05

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.

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Milde, Bastian; Pawliczek, Martin; Jones, Peter G.; Werz, Daniel B. (2017). Enantioselective Total Synthesis of (+)-Lysergol: A Formal anti‑Carbopalladation/Heck Cascade as the Key Step. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.7b00675

https://doi.org/10.1021/acs.orglett.7b00675

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