Total Synthesis of an Anti‐ Helicobacter pylori  Agent, Actinopyrone A | Zendy

Hosokawa Seijiro | Zendy; Yokota Kazuya | Zendy; Imamura Keisuke | Zendy; Suzuki Yasuaki | Zendy; Kawarasaki Masataka | Zendy; Tatsuta Kuniaki | Zendy

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Total Synthesis of an Anti‐ Helicobacter pylori Agent, Actinopyrone A

Author(s) -

Hosokawa Seijiro,

Yokota Kazuya,

Imamura Keisuke,

Suzuki Yasuaki,

Kawarasaki Masataka,

Tatsuta Kuniaki

Publication year - 2008

Publication title -

chemistry – an asian journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.18

H-Index - 106

eISSN - 1861-471X

pISSN - 1861-4728

DOI - 10.1002/asia.200800109

Subject(s) - phosphonate , helicobacter pylori , aldol reaction , silyl ether , absolute configuration , stereochemistry , ether , chemistry , sulfone , silylation , organic chemistry , catalysis , biology , genetics

Actinopyrone A, an anti‐ Helicobacter pylori agent, was synthesized in nine steps from a silyl dienol ether. A vinylogous anti ‐aldol was stereoselectively synthesized by our developed remote stereoinduction methodology; coupling of this with a sulfone and a phosphonate species led to the construction of a vinylpyrone compound. This was submitted to reductive de‐conjugation to give actinopyrone A. The absolute stereochemistry of actinopyrone A was determined to have the configuration 14 R ,15 R .

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