TY - JOUR
T1 - Stereodivergent Synthesis and Configurational Assignment of the C1-C15 Segment of Amphirionin-5
AU - Kanto, Moemi
AU - Sato, Sota
AU - Tsuda, Masashi
AU - Sasaki, Makoto
N1 - Funding Information:
We thank Professor Hiroyuki Isobe (The University of Tokyo, Tohoku University, ERATO JST) and Dr. Midori Oinuma (Tohoku University, ERATO JST) for NMR measurements, and Professor Haruhiko Fuwa (Tohoku University) and Dr. Kotaro Iwasaki (Tohoku University) for helpful discussions. This work was financially supported in part by JSPS KAKENHI Grant Nos. JP16K13082, JP16H01126 in Middle Molecular Strategy, JP23102016,42 and JP25282228.
Publisher Copyright:
© 2016 American Chemical Society.
PY - 2016/10/7
Y1 - 2016/10/7
N2 - The relative configuration of the C3-C12 portion of amphirionin-5, a novel marine polyketide with potent cell proliferation-promoting activity, was established by the stereodivergent synthesis of six diastereomeric model compounds and comparison of their NMR spectroscopic data with those reported for the natural product. This study led to the elucidation of the relative configuration between C4/C5 and C9/C12 and to the reassignment of the proposed configuration of the C9 position of amphirionin-5.
AB - The relative configuration of the C3-C12 portion of amphirionin-5, a novel marine polyketide with potent cell proliferation-promoting activity, was established by the stereodivergent synthesis of six diastereomeric model compounds and comparison of their NMR spectroscopic data with those reported for the natural product. This study led to the elucidation of the relative configuration between C4/C5 and C9/C12 and to the reassignment of the proposed configuration of the C9 position of amphirionin-5.
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U2 - 10.1021/acs.joc.6b01700
DO - 10.1021/acs.joc.6b01700
M3 - Article
C2 - 27564777
AN - SCOPUS:84990964632
SN - 0022-3263
VL - 81
SP - 9105
EP - 9121
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 19
ER -
