Total Synthesis of Neuroprotectin D1 Analogues Derived from Omega‑6 Docosapentaenoic Acid (DPA) and Adrenic Acid (AdA) from a Common Pivotal, Late-Stage Intermediate. - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2014

Total Synthesis of Neuroprotectin D1 Analogues Derived from Omega‑6 Docosapentaenoic Acid (DPA) and Adrenic Acid (AdA) from a Common Pivotal, Late-Stage Intermediate.

Résumé

The first total synthesis of three omega-6 dihydroxylated (E,E,Z)-docosatrienes has been successfully achieved employing a flexible strategy. The key features encompass a Boland semireduction, to create the (E,E,Z)-triene via an (E,E)-ynediene, and a selective deprotection of a tris(tert-butyldimethylsilyl) ether. The main advantage of the present strategy over previous syntheses of noncyclic dihydroxylated PUFA metabolites derived from docosahexaenoic and arachidonic acids comes from the introduction of the polar head chain at the very end of the synthesis from an advanced, pivotal aldehyde. In terms of divergency this enables late-stage modification of the head group.
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Dates et versions

hal-00996845 , version 1 (27-05-2014)

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Gandrath Dayaker, Thierry Durand, Laurence Balas. Total Synthesis of Neuroprotectin D1 Analogues Derived from Omega‑6 Docosapentaenoic Acid (DPA) and Adrenic Acid (AdA) from a Common Pivotal, Late-Stage Intermediate.. Journal of Organic Chemistry, 2014, 79 (6), pp.2657-2665. ⟨10.1021/jo500147r⟩. ⟨hal-00996845⟩
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