Total synthesis of resolvin D3.

Ogawa, Narihito; Katagiri, Kyosuke; Haimoto, Yosuke; Kobayashi, Yuichi

Ogawa, Narihito; Katagiri, Kyosuke; Haimoto, Yosuke; Kobayashi, Yuichi.

Afiliación

Ogawa N; Department of Applied Chemistry, Meiji University, 1-1-1, Higashimita, Tama-ku, Kawasaki, Kanagawa 214-8571, Japan. narihito@meiji.ac.jp.
Katagiri K; Department of Applied Chemistry, Meiji University, 1-1-1, Higashimita, Tama-ku, Kawasaki, Kanagawa 214-8571, Japan. narihito@meiji.ac.jp.
Haimoto Y; Department of Applied Chemistry, Meiji University, 1-1-1, Higashimita, Tama-ku, Kawasaki, Kanagawa 214-8571, Japan. narihito@meiji.ac.jp.
Kobayashi Y; Organization for the Strategic Coordination of Research and Intellectual Properties, Meiji University, 1-1-1, Higashimita, Tama-ku, Kawasaki, Kanagawa 214-8571, Japan.

Org Biomol Chem ; 20(21): 4338-4341, 2022 06 01.

Article en En | MEDLINE | ID: mdl-35551327

ABSTRACT

ABSTRACT

Resolvin D3 was synthesized by the Suzuki-Miyaura cross-coupling reaction of C1-C8 borane with C9-C22 iodoolefin as the key reaction. The latter intermediate was obtained by the sequential Wittig reactions of C9-C13 phosphonium salt with C14-C19 aldehyde and then C9-C19 aldehyde with propyltriphenylphosphonium bromide. The stereogenic centers at C4, C11, and C17 were constructed by the ruthenium-catalyzed asymmetric transfer hydrogenation with high stereoselectivity.

Asunto(s)

Aldehídos; Ácidos Grasos Insaturados; Hidrogenación; Estereoisomerismo

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Aldehídos / Ácidos Grasos Insaturados Idioma: En Revista: Org Biomol Chem Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2022 Tipo del documento: Article País de afiliación: Japón

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