Total Synthesis of (±)-Cochlearol A

Autor: Wen-Dan Xu, Dong Chen, Da-Wei Zhang, Hao-Miao Liu, Hong-Bo Qin, Dan-Dan Liu, Hui-Lan Fan
Rok vydání: 2019
Předmět:
Zdroj: Organic Letters. 21:6761-6764
ISSN: 1523-7052
1523-7060
DOI: 10.1021/acs.orglett.9b02391
Popis: Total synthesis of (±)-cochlearol A was accomplished, which features a cis 6/6 B/D ring synthesis. A TMSOTf-promoted lactonization of tert-butoxy ketoester produced the desired lactone with quaternary carbon. The cis configuration of the B/E ring is essential for regioselective B/D ring formation. Finally, simple deprotections and transformations gave cochlearol A in 16 steps from known ethyl 4-tert-butoxyacetoacetate.
Databáze: OpenAIRE