Total Synthesis of Polysubstituted γ-Butyrolactone Lignans (-)-Hinokinin, (-)-Bicubebin B, and (-)-Isodeoxypodophyllotoxin via Oxime Carbonate Formation.

Autor: Bobek KB; Department of Chemistry, University of Central Florida, Orlando, Florida 32816, United States., Ezzat NS; Department of Chemistry, University of Central Florida, Orlando, Florida 32816, United States.; Department of Chemistry, University of Mosul, Al Majmoaa St., Mosul 41002, Iraq., Jones BS; Department of Chemistry, University of Central Florida, Orlando, Florida 32816, United States., Bian Y; Department of Chemistry, University of Central Florida, Orlando, Florida 32816, United States., Shaw TE; Department of Chemistry, University of Central Florida, Orlando, Florida 32816, United States., Jurca T; Department of Chemistry, University of Central Florida, Orlando, Florida 32816, United States., Li H; Department of Chemistry, University of Central Florida, Orlando, Florida 32816, United States.; College of Life Sciences, Hebei Agricultural University, Baoding, Hebei 071000, P.R. China., Yuan Y; Department of Chemistry, University of Central Florida, Orlando, Florida 32816, United States.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2023 Jan 13; Vol. 25 (1), pp. 31-36. Date of Electronic Publication: 2022 Dec 23.
DOI: 10.1021/acs.orglett.2c03727
Abstrakt: The diverse structures and profound biological activities of lignan natural products have enticed significant effort in the exploration of new methodologies for their total synthesis. We have prepared γ-butyrolactone oximes from readily available δ-nitro alcohols via Boc 2 O mediated cyclization. The mild conditions are compatible with a wide range of functional groups, and this methodology has been applied to the total synthesis of five lignan natural products.
Databáze: MEDLINE