Total Synthesis of Liangshanone.
Angew Chem Int Ed Engl
; 59(52): 23609-23614, 2020 12 21.
Article
em En
| MEDLINE
| ID: mdl-32902096
The first total synthesis of liangshanone, a hexacyclic ent-kaurane diterpenoid alkaloid, has been completed. Its intricate cagelike framework was assembled through several key transformations, including an oxidative dearomatization/Diels-Alder (OD/DA) cycloaddition sequence, a tandem alkene cleavage/Mannich cyclization, a Robinson-type annulation, and an intramolecular aldol reaction. Notably, an organocatalytic enantioselective α-hydroxymethylation process allowed the preparation of an enantiomerically enriched tricyclic intermediate that should enable asymmetric access to the target natural product.
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MEDLINE
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En
Ano de publicação:
2020
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Article