TY - JOUR
T1 - Complete Stereochemical Assignment of Campechic Acids A and B
AU - Isaka, Ruri
AU - Yu, Linkai
AU - Sasaki, Makoto
AU - Igarashi, Yasuhiro
AU - Fuwa, Haruhiko
N1 - Publisher Copyright:
© 2016 American Chemical Society.
PY - 2016/5/6
Y1 - 2016/5/6
N2 - Campechic acids A and B are anti-invasive polyketide antibiotics isolated from Streptomyces sp. CHI93 strain. Herein we describe stereoselective synthesis of the C-16-C-30 fragment of campechic acids A and B via a biosynthesis-inspired epoxide-opening cascade and its NMR spectroscopic comparison with the authentic degradation product, resulting in configurational assignment of the C-21, C-24, C-25, and C-28 stereogenic centers and reassignment of the C-18 stereogenic center.
AB - Campechic acids A and B are anti-invasive polyketide antibiotics isolated from Streptomyces sp. CHI93 strain. Herein we describe stereoselective synthesis of the C-16-C-30 fragment of campechic acids A and B via a biosynthesis-inspired epoxide-opening cascade and its NMR spectroscopic comparison with the authentic degradation product, resulting in configurational assignment of the C-21, C-24, C-25, and C-28 stereogenic centers and reassignment of the C-18 stereogenic center.
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U2 - 10.1021/acs.joc.6b00290
DO - 10.1021/acs.joc.6b00290
M3 - Article
C2 - 27045676
AN - SCOPUS:84968779388
SN - 0022-3263
VL - 81
SP - 3638
EP - 3647
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 9
ER -