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Efficient Synthesis of a Styryl Analogue of (2S,3R,4E)-N2-Octadecanoyl-4-tetradecasphingenine via Cross-Metathesis Reaction

✍ Scribed by Gulshan Kumar; Sukhbir Kaur; Vasundhara Singh

Publisher
John Wiley and Sons
Year
2011
Tongue
German
Weight
156 KB
Volume
94
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The first total synthesis of sphingolipid (2__S__,3__R__,4__E__)‐N^2^‐octadecanoyl‐4‐tetradecasphingenine (1a), a natural sphingolipid isolated from Bombycis Corpus 101A, and of its styryl analogue 1b was achieved in good overall yield (Schemes 1 and 2). The key step involved the installation with (E) stereoselectivity of a long lipophilic chain or phenyl group on allyl alcohol derivative 3 via a cross‐metathesis reaction (→5a or 5b). The N‐Boc protected 3 was easily accessible from (S)‐Garner aldehyde.

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