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

Isao Kadota; Hiroyoshi Takamura; Kumi Sato; Yoshinori Yamamoto

doi:10.1021/jo025566f

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

Isao Kadota, Hiroyoshi Takamura, Kumi Sato, Yoshinori Yamamoto

Research output: Contribution to journal › Article › peer-review

45 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	3494-3498
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	67
Issue number	10
DOIs	https://doi.org/10.1021/jo025566f
Publication status	Published - May 17 2002
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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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. / Kadota, Isao ; Takamura, Hiroyoshi; Sato, Kumi; Yamamoto, Yoshinori.

In: Journal of Organic Chemistry, Vol. 67, No. 10, 17.05.2002, p. 3494-3498.

Research output: Contribution to journal › Article › peer-review

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AU - Yamamoto, Yoshinori

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