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Total synthesis ofN,O,O,O-tetraacetyl-d-ribo-phytosphingosine and its 2-epi-congener

✍ Scribed by Martinková, Miroslava; Pomikalová, Kvetoslava; Gonda, Jozef

Book ID: 119932367
Publisher: Versita
Year: 2013
Tongue: English
Weight: 252 KB
Volume: 67
Category: Article
ISSN: 0366-6352
DOI: 10.2478/s11696-012-0245-0

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✦ Synopsis

Abstract

Total synthesis of the natural d-ribo-phytosphingosine I and its 2-epimer III in the protected form was achieved through a common strategy. The aza-Claisen rearrangement of allylic thiocyanate (Z)-V incorporated the new stereogenic centre with nitrogen and the subsequent Wittig olefination constructed a non-polar side chain. Hydrogenation, followed by removal of protecting groups, completed the syntheses of I and III.

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