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 - 1994/5
Y1 - 1994/5
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.
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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 -