An Intramolecular Para-Phenolic Allylation Free Radical Cyclization Strategy for the Synthesis of Alkaloids and Terpenes With Spiro[4.5] Decane Architectures
Chemistry and Biochemistry
A Tsuji-Trost variant of the Winstein-Masamune reaction has been investigated for the synthesis of the AC spirocyclic ring system 9bearing a quaternary carbon found in the fawcettimine type Lycopodiumalkaloids magellanine 1 and lycojaponicumin B 2 and cyclopiane diterpenes such as conidiogenone 3. Annulation of the B ring for the synthesis of tricyclic ABC cores was demonstrated utilizing a 5-exo-trig free radical cyclization of a primary carbon radical onto a cyclohexadienone generated with tri-n-butylgermanium hydride (9 → 11).
Donahue, M. G.,
Jentsch, N. G.,
Realini, E. C.
(2017). An Intramolecular Para-Phenolic Allylation Free Radical Cyclization Strategy for the Synthesis of Alkaloids and Terpenes With Spiro[4.5] Decane Architectures. Tetrahedron Letters, 58(33), 3219-3222.
Available at: https://aquila.usm.edu/fac_pubs/14901