TY - JOUR
T1 - Toward the Creation of Induced Pluripotent Small (iPS) Molecules
T2 - Establishment of a Modular Synthetic Strategy for the Heronamide C-type Polyene Macrolactams and Their Conformational and Reactivity Analysis
AU - Kanoh, Naoki
AU - Terajima, Yuta
AU - Tanaka, Suguru
AU - Terashima, Ryusei
AU - Nishiyama, Hiromichi
AU - Nagasawa, Shota
AU - Sasano, Yusuke
AU - Iwabuchi, Yoshiharu
AU - Nishimura, Shinichi
AU - Kakeya, Hideaki
N1 - Funding Information:
This work was supported in part by Grants-in-Aid for Scientific Research on Innovative Areas from the Ministry of Education, Culture, Sports, Science, and Technology, Japan (17H06401 to H.K. and 18H04603 to N.K.); a Grant-in-Aid for Scientific Research (C) from the Japan Society for the Promotion of Science (19K06990 to N.K.); and a grant from the Tokyo Biochemical Research Foundation to N.K.
Publisher Copyright:
© 2021 American Chemical Society.
PY - 2021/12/3
Y1 - 2021/12/3
N2 - A highly modular synthetic strategy for the heronamide C-type polyene macrolactams was established by synthesizing 8-deoxyheronamide C (2). The developed strategy enabled not only the total synthesis of 8-deoxyheronamide C (2) but also the unified synthesis of four heronamide-like molecules named "heronamidoids"(5-8). Conformational and reactivity analysis of the heronamidoids clarified that (1) the C19 stereochemistry mainly affected the conformation of the amide linkage, resulting in the change of alignment of two polyene units and reactivity toward photochemical [6π+ 6π] cycloaddition, and (2) the C8,C9-diol moiety is important for the conversion to the heronamide A-type skeleton from the heronamide C skeleton.
AB - A highly modular synthetic strategy for the heronamide C-type polyene macrolactams was established by synthesizing 8-deoxyheronamide C (2). The developed strategy enabled not only the total synthesis of 8-deoxyheronamide C (2) but also the unified synthesis of four heronamide-like molecules named "heronamidoids"(5-8). Conformational and reactivity analysis of the heronamidoids clarified that (1) the C19 stereochemistry mainly affected the conformation of the amide linkage, resulting in the change of alignment of two polyene units and reactivity toward photochemical [6π+ 6π] cycloaddition, and (2) the C8,C9-diol moiety is important for the conversion to the heronamide A-type skeleton from the heronamide C skeleton.
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U2 - 10.1021/acs.joc.1c01760
DO - 10.1021/acs.joc.1c01760
M3 - Article
AN - SCOPUS:85120075313
SN - 0022-3263
VL - 86
SP - 16231
EP - 16248
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 23
ER -