TY - JOUR
T1 - Unified total synthesis, stereostructural elucidation, and biological evaluation of sarcophytonolides
AU - Takamura, Hiroyoshi
AU - Kadota, Isao
N1 - Publisher Copyright:
© 2019 Society of Synthetic Organic Chemistry. All rights reserved.
Copyright:
Copyright 2020 Elsevier B.V., All rights reserved.
PY - 2019
Y1 - 2019
N2 - Sarcophytonolides are cembranolide diterpenes isolated from the soft corals of genus Sarcophyton since 2005. Herein, unified total synthesis of sarcophytonolides C, E, F, G, H, and J and isosarcophytonolide D is reported. The key transformations in the synthetic route are fragment coupling, alkoxycarbonylallylation, macrolactonization, and transannular ring - closing metathesis. These total syntheses resulted in the absolute stereochemical confirmation of sarcophytonolide H, determination 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 their key synthetic intermediates.
AB - Sarcophytonolides are cembranolide diterpenes isolated from the soft corals of genus Sarcophyton since 2005. Herein, unified total synthesis of sarcophytonolides C, E, F, G, H, and J and isosarcophytonolide D is reported. The key transformations in the synthetic route are fragment coupling, alkoxycarbonylallylation, macrolactonization, and transannular ring - closing metathesis. These total syntheses resulted in the absolute stereochemical confirmation of sarcophytonolide H, determination 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 their key synthetic intermediates.
KW - Alkoxycarbonylallylation
KW - Antifouling activity
KW - Biological evaluation
KW - Cembranolide
KW - Cytotoxity
KW - Diterpene
KW - Fragment coupling
KW - Macrolactonization
KW - Sarcophytonolide
KW - Structural elucidation
KW - Toxicity
KW - Transannular ring-closing metathesis
KW - Unified total synthesis
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U2 - 10.5059/yukigoseikyokaishi.77.1190
DO - 10.5059/yukigoseikyokaishi.77.1190
M3 - Article
AN - SCOPUS:85084921925
VL - 77
SP - 1190
EP - 1200
JO - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
JF - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
SN - 0037-9980
IS - 12
ER -