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Application of chiral tethers to intramolecular [2+2] photocycloadditions: synthetic approach to (−)-italicene and (+)-isoitalicene

✍ Scribed by Sophie Faure; Olivier Piva

Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 85 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)01933-x

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✦ Synopsis

A synthetic approach to ( -)-italicene and ( +)-isoitalicene, sesquiterpenes which possess the rare tricyclo[5.4.0.0 1,5 ] undecane skeleton has been developed using as key step a highly regio-and diastereoselective [2 +2] photocycloaddition. (S)-Lactic acid plays the role of a chiral removable tether group during the building of the cyclobutane ring.

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