TY - JOUR
T1 - Total synthesis of an anti-Helicobacter pylori agent, actinopyrone A
AU - Hosokawa, Seijiro
AU - Yokota, Kazuya
AU - Imamura, Keisuke
AU - Suzuki, Yasuaki
AU - Kawarasaki, Masataka
AU - Tatsuta, Kuniaki
PY - 2008/9/1
Y1 - 2008/9/1
N2 - 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 14R,15R.
AB - 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 14R,15R.
KW - Actinopyrone A
KW - Aldol reaction
KW - Remote stereoinduction
KW - Structural determination
KW - Total synthesis
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U2 - 10.1002/asia.200800109
DO - 10.1002/asia.200800109
M3 - Article
C2 - 18633953
AN - SCOPUS:54849426413
SN - 1861-4728
VL - 3
SP - 1415
EP - 1421
JO - Chemistry - An Asian Journal
JF - Chemistry - An Asian Journal
IS - 8-9
ER -