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Synthetic Studies Toward caphalotaxine: Functionalization of Tertiary N-Acylhemiaminals by Nazarov Cyclization
31 December 2000 (online)
Functionalization of bicyclic N-acylhemiaminals, which are readily available by titanium-mediated intramolecular coupling of vinyl-tethered imides, has been achieved by use of the Nazarov cyclization to construct the carbon-carbon bond at the quaternary center. This synthetic strategy allows rapid entry to the key structural elements of cephalotaxine.
low-valent titanium - imide - N-acylhemiaminal - quaternary center - Nazarov cyclization