Concise Synthesis of Cyclic Ethers via the Palladium-Catalyzed
Coupling of Ketene Acetal Triflates and Organozinc Reagents.
Application to the Iterative Synthesis of Polycyclic Ethers
posted on 2002-04-25, 00:00authored byIsao Kadota, Hiroyoshi Takamura, Kumi Sato, Yoshinori Yamamoto
The reaction of the ketene acetal triflates 9a−e and a zinc homoenolate 10 in the presence of a
catalytic amount of Pd(PPh3)4 gave the enol ethers 11a−e in good yields. The products were
converted to the corresponding cyclic ethers 14a and 14b by hydroboration and lactonization. The
present methodology allowed us to synthesize the DE and GH ring segment of gambierol in a concise
manner. Iterative syntheses of the polycyclic ethers 26 and 32 are also described.