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A simple convergent synthesis of trans-fused six-membered polycyclic ethers

โœ Scribed by Yuji Mori; Shinjiro Mitsuoka; Hiroshi Furukawa

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
160 KB
Volume
41
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

A highly convergent method for the synthesis of trans-fused polytetrahydropyrans was developed, which involves: (i) coupling of cyclic triflate with an acetylene unit; (ii) oxidation of acetylene to 1,2-diketone; (iii) formation of a trans-fused cyclic dihemiacetal; (iv) O-methylation of the dihemiacetal; and (v) stereoselective reduction of the diacetal to trans-fused oxane rings.

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Efficient strategy for convergent synthe
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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