Enantioselective total synthesis of the potent anti-inflammatory (+)-myrrhanol A.
The first total synthesis of potent anti-inflammatory polypodanes (+)-myrrhanol A (1), (+)-myrrhanone A (2), (+)-myrrhanone B (3), and (+)-myrrhanol B (4) has been achieved. Key steps in our convergent, highly stereocontrolled route are a Ti(III)-mediated radical cyclization of a chiral monoepoxide to furnish a bicyclic synthon that combines stereospecifically with an acyclic vinyl iodide via an intermolecular B-alkyl Suzuki-Miyaura cross-coupling.
Domingo
Victoriano
V
Department of Organic Chemistry, Institute of Biotechnology, University of Granada, Avda. Fuentenueva, 18071 Granada, Spain.
Silva
Lúcia
L
Diéguez
Horacio R
HR
Arteaga
Jesús F
JF
Quílez del Moral
José F
JF
Barrero
Alejandro F
AF
D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D003500:Cyclization; D013237:Stereoisomerism; D013379:Substrate Specificity; D014315:Triterpenes / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology
D000893:Anti-Inflammatory Agents; D014315:Triterpenes; C434796:myrrhanol A