Asymmetric Total Synthesis and Structure Elucidation of Huperzine H.
J Org Chem
; 87(5): 3730-3735, 2022 03 04.
Article
em En
| MEDLINE
| ID: mdl-35040311
ABSTRACT
A first asymmetric total synthesis of huperzine H has been achieved in a 12% overall yield from commercially available (+)-pulegone. The key steps of this synthesis include a highly diastereoselective Mukaiyama-Michael addition reaction of a pyrrole bearing a silyl enol ether and an intramolecular SN2 cyclization reaction with iodinated pyrrole acting as an effective nucleophile for the formation of the nine-membered ring. As a result, the relative and absolute stereochemistry of huperzine H is established.
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Idioma:
En
Ano de publicação:
2022
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Article