Abstract
: The BF3.OEt2 mediated cyclization of ω-tributylstannyl ether aldehyde 1 produces seven-membered cyclic ethers 2 in 95% yield with high diastereoselectivity (2a:2b = 93:7). Perfect stereocontrol between a and α’ proton is accomplished in the cyclization to give the cis products, and the stereochemistry between a and p proton is controlled to trans resulting in the predominant formation of the anti isomer 2a. This allylic tin method is applied to the stereocontrolled synthesis of 6,7,7,6-polycyclic ether skeleton as a model synthesis of brevetoxin B.
| Original language | English |
|---|---|
| Pages (from-to) | 269-289 |
| Number of pages | 21 |
| Journal | Main Group Metal Chemistry |
| Volume | 17 |
| Issue number | 1-4 |
| DOIs | |
| Publication status | Published - 1994 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Chemistry(all)
- Materials Chemistry
- Metals and Alloys
- Condensed Matter Physics
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Stereocontrolled synthesis of the 6-7-7-6 ring system of polycyclic ethers via the intramolecular reaction with ω-tributylstannyl ether aldehydes. / Kadota, Isao; Yamamoto, Yoshinori.
In: Main Group Metal Chemistry, Vol. 17, No. 1-4, 1994, p. 269-289.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Stereocontrolled synthesis of the 6-7-7-6 ring system of polycyclic ethers via the intramolecular reaction with ω-tributylstannyl ether aldehydes
AU - Kadota, Isao
AU - Yamamoto, Yoshinori
PY - 1994
Y1 - 1994
N2 - : The BF3.OEt2 mediated cyclization of ω-tributylstannyl ether aldehyde 1 produces seven-membered cyclic ethers 2 in 95% yield with high diastereoselectivity (2a:2b = 93:7). Perfect stereocontrol between a and α’ proton is accomplished in the cyclization to give the cis products, and the stereochemistry between a and p proton is controlled to trans resulting in the predominant formation of the anti isomer 2a. This allylic tin method is applied to the stereocontrolled synthesis of 6,7,7,6-polycyclic ether skeleton as a model synthesis of brevetoxin B.
AB - : The BF3.OEt2 mediated cyclization of ω-tributylstannyl ether aldehyde 1 produces seven-membered cyclic ethers 2 in 95% yield with high diastereoselectivity (2a:2b = 93:7). Perfect stereocontrol between a and α’ proton is accomplished in the cyclization to give the cis products, and the stereochemistry between a and p proton is controlled to trans resulting in the predominant formation of the anti isomer 2a. This allylic tin method is applied to the stereocontrolled synthesis of 6,7,7,6-polycyclic ether skeleton as a model synthesis of brevetoxin B.
UR - http://www.scopus.com/inward/record.url?scp=0042055632&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0042055632&partnerID=8YFLogxK
U2 - 10.1515/MGMC.1994.17.1-4.269
DO - 10.1515/MGMC.1994.17.1-4.269
M3 - Article
AN - SCOPUS:0042055632
VL - 17
SP - 269
EP - 289
JO - Reviews on silicon, germanium, tin and lead compounds
JF - Reviews on silicon, germanium, tin and lead compounds
SN - 0792-1241
IS - 1-4
ER -