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Stereoselective synthesis of MaR2_{n-3 DPA}.

ABSTRACT: The first total synthesis of the n-3 docosapentaenoic derived oxygenated product MaR2_{n-3 DPA} has been achieved. The 13R and 14S stereogenic centers were introduced using 2-deoxy-d-ribose in a chiral pool strategy. The geometry of the Z,E,E-triene moiety was prepared using highly E-selective Wittig- and Takai-olefination reactions as well as the Z-stereoselective Lindlar reduction. LC/MS-MS data of synthetic MaR2_{n-3 DPA} matched data for the biosynthetic formed product that enabled the configurational assignment of this oxygenated natural product to be (7Z,9E,11E,13R,14S,16Z,19Z)-13,14-dihydroxydocosa-7,9,11,16,19-pentaenoic acid.

SUBMITTER: Sonderskov J

PROVIDER: S-EPMC7709930 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

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Stereoselective synthesis of MaR2n-3 DPA.

Sønderskov Jeanne J Tungen Jørn E JE Palmas Francesco F Dalli Jesmond J Serhan Charles N CN Stenstrøm Yngve Y Hansen Trond Vidar TV

Tetrahedron letters 20191209 7

The first total synthesis of the n-3 docosapentaenoic derived oxygenated product MaR2n-3 DPA has been achieved. The 13R and 14S stereogenic centers were introduced using 2-deoxy-d-ribose in a chiral pool strategy. The geometry of the Z,E,E-triene moiety was prepared using highly E-selective Wittig- and Takai-olefination reactions as well as the Z-stereoselective Lindlar reduction. LC/MS-MS data of synthetic MaR2n-3 DPA ...[more]

PMID: 33273748

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