Efficient Synthesis of a Styryl Analogue of (2 S ,3 R ,4 E )‐ N  2 ‐Octadecanoyl‐4‐tetradecasphingenine  via  Cross‐Metathesis Reaction | Zendy

Kumar Gulshan | Zendy; Kaur Sukhbir | Zendy; Singh Vasundhara | Zendy

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

Author(s) -

Kumar Gulshan,

Kaur Sukhbir,

Singh Vasundhara

Publication year - 2011

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.201000277

Subject(s) - chemistry , metathesis , stereoselectivity , aldehyde , derivative (finance) , yield (engineering) , stereochemistry , alcohol , salt metathesis reaction , allyl alcohol , combinatorial chemistry , organic chemistry , catalysis , polymer , materials science , financial economics , economics , polymerization , metallurgy

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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