Polycyclic framework synthesis of anominine and tubingensin A indole diterpenoids.
A highly congested decalin embodying an alpha-methylene ketone is synthesized in 11 steps from the Wieland-Miescher ketone and efficiently converted to the polycyclic frameworks of anominine and tubingensin A, which constitutes the first approach to the skeleton of these indole diterpenoids.
Bradshaw
Ben
B
Laboratori de Química Orgànica, Facultat de Farmàcia, Institut de Biomedicina (IBUB), Universitat de Barcelona, Av. Joan XXIII s/n, 08028-Barcelona, Spain.
Etxebarria-Jardí
Gorka
G
Bonjoch
Josep
J
D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D009281:Naphthalenes / Q000138:chemical synthesis / Q000737:chemistry; D011083:Polycyclic Compounds / Q000737:chemistry*
D004224:Diterpenes; D007211:Indoles; D007659:Ketones; D009281:Naphthalenes; D011083:Polycyclic Compounds; C007229:decalin