Synthesis of the oxazolidinone fragment of thelepamide.

Synthesis of the oxazolidinone fragment of thelepamide.
Nat Prod Res. 2020 Aug 31;:1-7
Authors: Ashida N, Ida K, Koide Y, Vavricka CJ, Izumi M, Kiyota H
Abstract
Thelepamide, an unique ketide-amino acid isolated from a marine annelid worm Thelepus crispus, has a unique oxazolidinone ring derived from cysteine, glycine and valine. Rareness in nature as well as promising bioactive possibility make the oxazolidinone ring an attractive synthetic target. The hydroxy oxazolidinone fragment of thelepamide was prepared by acid-catalysed N,O-acetal formation between a ketoamide and formaldehyde. Lactone-carbonyl selective isopropyl addition to an oxazilidine-dione under Grignard conditions also forms the target compound.
PMID: 32865028 [PubMed - as supplied by publisher]

Source: Natural Product Research - August 30, 2020 Category: Biochemistry Authors: Ashida N, Ida K, Koide Y, Vavricka CJ, Izumi M, Kiyota H Tags: Nat Prod Res Source Type: research