DDQ-Catalyzed Oxidative C(sp3)-H Functionalization of Aryltetralins and Subsequent Chemoselective Oxidative Demethylation to Access Dihydronaphthalenes and Dihydronaphthoquinones.
J Org Chem
; 86(21): 15096-15116, 2021 Nov 05.
Article
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| MEDLINE
| ID: mdl-34586815
ABSTRACT
A highly controlled DDQ-catalyzed oxidative C(sp3)-H functionalization of three contiguous carbon atoms in aryltetralins is reported for efficient access to diverse oxygenated dihydronaphthalene scaffolds. The first total synthesis of pachypostaudin B is realized. Further, a CAN-mediated chemoselective oxidative demethylation on the dihydronaphthalene scaffolds is demonstrated to arrive at the rarely observed dihydronaphthoquinone core in moderate to good yields. The present methodology enables quick access to a library of magnoshinin and merrilliaquinone analogs.
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MEDLINE
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En
Revista:
J Org Chem
Año:
2021
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Article
País de afiliación:
India