A Convergent Hetero‐Diels–Alder Strategy for Asymmetric Access to a Lactone Containing Two Lipidic Chains | Zendy

Vu Cong S. | Zendy; Guisot Nicolas | Zendy; Guillarme Stéphane | Zendy; Martel Arnaud | Zendy; Dujardin Gilles | Zendy; Pipelier Muriel | Zendy; Dubreuil Didier | Zendy; Saluzzo Christine | Zendy

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A Convergent Hetero‐Diels–Alder Strategy for Asymmetric Access to a Lactone Containing Two Lipidic Chains

Author(s) -

Vu Cong S.,

Guisot Nicolas,

Guillarme Stéphane,

Martel Arnaud,

Dujardin Gilles,

Pipelier Muriel,

Dubreuil Didier,

Saluzzo Christine

Publication year - 2012

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201200513

Subject(s) - chemistry , lactone , adduct , yield (engineering) , alkyl , diels–alder reaction , ceramide , surface modification , organic chemistry , catalysis , stereochemistry , biochemistry , apoptosis , materials science , metallurgy

Eu(fod) 3 ‐catalyzed heterocycloaddition of chiral β‐alkyl‐ N ‐vinyl‐1,3‐oxazolidin‐2‐ones with a heterodiene bearing a lipidic chain led to heterocycloadducts in high yield with excellent endo and facial selectivities. An original lipidic lactone, a potent precursor of a ceramide analog, was obtained in seven steps from the adduct in a convergent manner after appropriate functionalization.

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