Expedient construction of the vibsanin E core without the use of protecting groups.
[reaction: see text] The tricyclic core of vibsanin E was constructed without the use of a protecting group in six steps. The El Gaïed Baylis-Hillman variant was key to allowing the Brønsted acid induced tandem cyclization forming rings B and C in one operation.
Heim
Ralf
R
School of Molecular and Microbial Sciences, University of Queensland, St. Lucia, 4072 Queensland, Australia.
Wiedemann
Stefan
S
Williams
Craig M
CM
Bernhardt
Paul V
PV
D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D027925:Viburnum / Q000737:chemistry
D004224:Diterpenes; C506848:vibsanin E