Enantioselective Total Synthesis of the Marine Macrolides Salarins A and C.
J Am Chem Soc
; 146(12): 8456-8463, 2024 03 27.
Article
em En
| MEDLINE
| ID: mdl-38479352
ABSTRACT
Here we report the first total synthesis of the marine macrolide salarin C, a potent anticancer agent, and demonstrate the biomimetic oxidation-Wasserman rearrangement to access salarin A. This synthesis relies on L-proline catalysis to install a chlorohydrin function that masks the sensitive C16-C17 epoxide and potentially mimics the biosynthesis of these compounds where a related chlorohydrin may yield both THF- and epoxide-containing salarins. Additional and key features of the synthesis include (i) macrocycle formation via ring-closing metathesis, (ii) macrocyclic substrate-controlled epoxidation of the C12-C13 allylic alcohol, and (iii) a late-stage Julia-Kocienski olefination to install the side chain. Importantly, this work provides a platform for the synthesis of other salarins and analogues of these potentially important anticancer natural products.
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1
Base de dados:
MEDLINE
Assunto principal:
Cloridrinas
/
Antineoplásicos
Idioma:
En
Ano de publicação:
2024
Tipo de documento:
Article