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Further study on SmI2-induced reductive intramolecular cyclization: synthesis of polycyclic ethers having an angular methyl group

โœ Scribed by Keisuke Suzuki; Hiroko Matsukura; Goh Matsuo; Hiroyuki Koshino; Tadashi Nakata


Book ID
104252347
Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
132 KB
Volume
43
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


The SmI 2 -induced reductive intramolecular cyclization of an aldehyde and b-alkoxy acrylate was further investigated for the synthesis of polycyclic ethers having an angular methyl group. The cyclization produced 6,6-and 6,7-membered bicyclic ethers having a methyl group at C2 or C6 and C2 or C7 position, respectively.


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An efficient convergent strategy for the construction of a trans-fused 6-6-6-6-membered tetracyclic ether ring system was developed. The key steps involve coupling of two cyclic ethers by esterification, SmI 2 -promoted intramolecular reductive cyclization of iodo ester to hemiacetal, dehydration to