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Efficient strategy for convergent synthesis of trans-fused polycyclic ethers based on an intramolecular SmI2-promoted cyclization of iodo ester

✍ Scribed by Koji Kawamura; Hiroshi Hinou; Goh Matsuo; Tadashi Nakata

Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 131 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(03)01277-2

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✦ Synopsis

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 dihydropyran, hydroboration, oxidation, intramolecular acetalization, and Lewis-acid catalyzed silane reduction.

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