期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 8, 页码 2490-2494出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201813090
关键词
aldol; cascade; gold; natural products; total synthesis
资金
- ETH Zurich
- Stipendienfonds Schweizerische Chemische Industrie (SSCI)
The first asymmetric total synthesis of the meroterpenoid (-)-merochlorin A is described. The route features enantiospecific gold-catalyzed tandem 1,3-acyloxy migration/Nazarov/aldol reaction sequence to furnish the bicyclo[3.3.0]octane core in a single step from a linear propargylic 1,3-enyne aldehyde. After completion of the central skeleton by reductive enol lactone rearrangement, late stage Diels-Alder cycloaddition/aromatization sequence installed the resorcinol. An additional salient feature of the synthesis is the assignment of the absolute configuration, which had not been determined previously.
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