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Facile transformation of 2-azetidinones to unsaturated ketones: application to the formal synthesis of sphingosine and phytosphingosine

✍ Scribed by Hyeon Kyu Lee; Eun-Kyung Kim; Chwang Siek Pak

Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 149 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)02444-9

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✦ Synopsis

2-Azetidinones were smoothly transformed to unsaturated ketones through the ring opening of activated 2-azetidinone by phosphonate stabilized carbanion and subsequent Horner-Wadsworth-Emmons olefination of the resulting b-ketophosphonates with aldehydes. A formal synthesis of L-erythro -sphingosine and D-lyxo -phytosphingosine from readily available 2-azetidinone was established utilizing this methodology.

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