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 journalArticle

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 languageEnglish
Pages (from-to)3494-3498
Number of pages5
JournalJournal of Organic Chemistry
Volume67
Issue number10
DOIs
Publication statusPublished - May 17 2002
Externally publishedYes

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Cyclic Ethers
Acetals
Ethers
Palladium
Zinc
ketene

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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T1 - 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

AU - Kadota, Isao

AU - Takamura, Hiroyoshi

AU - Sato, Kumi

AU - Yamamoto, Yoshinori

PY - 2002/5/17

Y1 - 2002/5/17

N2 - 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.

AB - 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.

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