An Intramolecular Para-Phenolic Allylation Free Radical Cyclization Strategy for the Synthesis of Alkaloids and Terpenes With Spiro[4.5]decane Architectures
Document Type
Article
Publication Date
1-1-2017
Department
Chemistry and Biochemistry
School
Mathematics and Natural Sciences
Abstract
© 2017 Elsevier Ltd. A Tsuji-Trost variant of the Winstein-Masamune reaction has been investigated for the synthesis of the AC spirocyclic ring system 9 bearing a quaternary carbon found in the fawcettimine type Lycopodium alkaloids 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).
Publication Title
Tetrahedron Letters
Volume
58
Issue
33
First Page
3219
Last Page
3222
Recommended Citation
Donahue, M.,
Jentsch, N.,
Realini, E.
(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/18453