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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 .