TY - JOUR
T1 - Unified Total Synthesis, Stereostructural Elucidation, and Biological Evaluation of Sarcophytonolides
AU - Takamura, Hiroyoshi
AU - Kikuchi, Takahiro
AU - Iwamoto, Kohei
AU - Nakao, Eiji
AU - Harada, Naoki
AU - Otsu, Taichi
AU - Endo, Noriyuki
AU - Fukuda, Yuji
AU - Ohno, Osamu
AU - Suenaga, Kiyotake
AU - Guo, Yue Wei
AU - Kadota, Isao
N1 - Funding Information:
We are grateful to Ms. Miyuki Uni (Okayama University) for her contribution during the early stage of the study, Professor Ichiro Hayakawa (Okayama University) for valuable discussion on the conformational analysis, and the Division of Instrumental Analysis Okayama University, for the NMR measurements. We appreciate The Yakumo Foundation for Environmental Science for financial support. This research was supported by JSPS KAKENHI Grant Number 17K05862.
Publisher Copyright:
Copyright © 2018 American Chemical Society.
PY - 2018/9/21
Y1 - 2018/9/21
N2 - Sarcophytonolides are cembranolide diterpenes isolated from the soft corals of genus Sarcophyton. Unified total synthesis of sarcophytonolides C, E, F, G, H, and J and isosarcophytonolide D was achieved. The synthetic routes feature NaHMDS- or SmI2-mediated fragment coupling, alkoxycarbonylallylation, macrolactonization, and transannular ring-closing metathesis. These total syntheses led to the absolute configurational confirmation of sarcophytonolide H, elucidation of sarcophytonolides C, E, F, and G, and revision of sarcophytonolide J and isosarcophytonolide D. We also evaluated the antifouling activity and toxicity of the synthetic sarcophytonolides H and J and their analogues as well as the cytotoxicity of the synthetic sarcophytonolides and the key synthetic intermediates.
AB - Sarcophytonolides are cembranolide diterpenes isolated from the soft corals of genus Sarcophyton. Unified total synthesis of sarcophytonolides C, E, F, G, H, and J and isosarcophytonolide D was achieved. The synthetic routes feature NaHMDS- or SmI2-mediated fragment coupling, alkoxycarbonylallylation, macrolactonization, and transannular ring-closing metathesis. These total syntheses led to the absolute configurational confirmation of sarcophytonolide H, elucidation of sarcophytonolides C, E, F, and G, and revision of sarcophytonolide J and isosarcophytonolide D. We also evaluated the antifouling activity and toxicity of the synthetic sarcophytonolides H and J and their analogues as well as the cytotoxicity of the synthetic sarcophytonolides and the key synthetic intermediates.
UR - http://www.scopus.com/inward/record.url?scp=85052320629&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85052320629&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.8b01634
DO - 10.1021/acs.joc.8b01634
M3 - Article
C2 - 30091605
AN - SCOPUS:85052320629
SN - 0022-3263
VL - 83
SP - 11028
EP - 11056
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 18
ER -