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 | |
| Publication status | Published - May 17 2002 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
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
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TY - JOUR
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.
UR - http://www.scopus.com/inward/record.url?scp=0037123627&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0037123627&partnerID=8YFLogxK
U2 - 10.1021/jo025566f
DO - 10.1021/jo025566f
M3 - Article
C2 - 12003565
AN - SCOPUS:0037123627
VL - 67
SP - 3494
EP - 3498
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 10
ER -