Nicholas Reactions of Pentadiynyl–Co₂(CO)₆ Cations. Synthesis of Antimalarial Hinokiresinol Analogues

Abstract

Penta-1,4-diyn-3-ol–Co₂(CO)₆ complexes undergo Lewis acid mediated Nicholas reactions with high selectivity at the C-3 site, to give skipped (1,4-)diyne complexes. The compatible nucleophiles have a wide range of reactivity. The methodology has been applied to the synthesis of both (E)- and (Z)-isomers of a hinokiresinol and nyasol analogue, the (E)-isomer of which is known to have elevated antiplasmodial and antimalarial activity.

Key words

propargyl - carbocations - alkyne complexes - diynes - Lewis acids - norneolignans - antimalarial agents

Publication History

Received: 18 September 2023

Accepted after revision: 22 January 2024

Accepted Manuscript online:
22 January 2024

Article published online:
14 February 2024

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