Total Syntheses of Aflavazole and 14-Hydroxyaflavinine
2016; American Chemical Society; Volume: 138; Issue: 48 Linguagem: Inglês
10.1021/jacs.6b10880
ISSN1943-2984
AutoresHailong Li, Qi‐Feng Chen, Zhaohong Lu, Ang Li,
Tópico(s)Marine Sponges and Natural Products
ResumoThe first total syntheses of aflavazole (6) and 14-hydroxyaflavinine (8), two sterically congested indole diterpenoids, were accomplished. AlI3-promoted alkyne Prins cyclization was exploited to construct their key structural motifs. An electrocyclization-aromatization sequence assembled the pentasubstituted arene of 6, and a Stille-Migita coupling furnished the tetrasubstituted olefin of 8. The benzylic and allylic C-O bonds were reductively cleaved at the late stage of the syntheses, respectively.
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