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Stereoselective construction of the ring system of robustadials

✍ Scribed by Marek Majewski; Gary Bantle

Publisher: Elsevier Science
Year: 1989
Tongue: French
Weight: 261 KB
Volume: 30
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)70642-3

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✦ Synopsis

The spiro [3,4-dihydro-2H-l-benzopyran-2,2'-bicyclo[3,l.l]heptane] framework of natural products Robustadials was constructed in a homochiral form. The synthesis started from lS-(-)-p-pinene, which was coupled to a substituted benzaldehyde using a Prins reaction, and incorporated a diastereoselective, Michael-type, intramolecular addition.

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