Methylene C(sp3 )-H Arylation Enables the Stereoselective Synthesis and Structure Revision of Indidene Natural Products.
Angew Chem Int Ed Engl
; 63(1): e202316103, 2024 Jan 02.
Article
em En
| MEDLINE
| ID: mdl-37997293
ABSTRACT
The divergent synthesis of two indane polyketides of the indidene family, namely (±)-indidene A (11 steps, 1.7 %) and (+)-indidene C (13 steps, 1.3 %), is reported. The synthesis of the trans-configured common indane intermediate was enabled by palladium(0)-catalyzed methylene C(sp3 )-H arylation, which was performed in both racemic and enantioselective (e.r. 99 1) modes. Further elaboration of this common intermediate by nickel-catalyzed dehydrogenative coupling allowed the rapid installation of the aroyl moiety of (±)-indidene A. In parallel, the biphenyl system of (±)- and (+)-indidene C was constructed by Suzuki-Miyaura coupling. These investigations led us to revise the structures of indidenes B and C.
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01-internacional
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MEDLINE
Idioma:
En
Revista:
Angew Chem Int Ed Engl
Ano de publicação:
2024
Tipo de documento:
Article
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