著者 Takamura, Hiroyoshi| Kikuchi, Takahiro| Iwamoto, Kohei| Nakao, Eiji| Harada, Naoki| Otsu, Taichi| Endo, Noriyuki| Fukuda, Yuji| Ohno, Osamu| Suenaga, Kiyotake| Guo, Yue-Wei| Kadota, Isao|
備考 This is an Accepted Manuscript of an article published by American Chemical Society This fulltext will be available in Aug 2019
発行日 2018-08-09
出版物タイトル The Journal of Organic Chemistry
83巻
18号
出版者 American Chemical Society
開始ページ 11028
終了ページ 11056
ISSN 0022-3263
NCID AA00704100
資料タイプ 学術雑誌論文
言語 English
OAI-PMH Set 岡山大学
論文のバージョン author
PubMed ID 30091605
DOI 10.1021/acs.joc.8b01634
関連URL isVersionOf https://doi.org/10.1021/acs.joc.8b01634
フルテキストURL tetrahed_lett_59_11_955.pdf
著者 Takamura, Hiroyoshi|
キーワード Natural product Stereodivergent synthesis Stereodiversification Stereoisomer
発行日 2018-02-10
出版物タイトル Tetrahedron Letters
59巻
11号
出版者 Pergamon Press
開始ページ 955
終了ページ 966
ISSN 00404039
NCID AA00861801
資料タイプ 学術雑誌論文
言語 English
OAI-PMH Set 岡山大学
論文のバージョン author
DOI 10.1016/j.tetlet.2018.02.004
関連URL isVersionOf https://doi.org/10.1016/j.tetlet.2018.02.004
フルテキストURL J_Org_Chem_80_6_3111.pdf
著者 Takamura, Hiroyoshi| Wada, Hiroko| Ogino, Mao| Kikuchi, Takahiro| Kadota, Isao| Uemura, Daisuke|
抄録 Four possible diastereomers of the C1-C13 fragment of symbiodinolide, which were proposed by the stereostructural analysis of the degraded product, were synthesized in a stereodivergent and stereoselective manner. The key transformations were aldol reaction of methyl acetoacetate with the aldehyde, diastereoselective reduction of the resulting β-hydroxy ketone, and the stereoinversion at the C6 position. Comparison of the (1)H NMR data between the four synthetic products and the degraded product revealed the relative stereostructure of the C1-C13 fragment of symbiodinolide.
備考 This is an Accepted Manuscript of an article published by American Chemical Society This research was supported by a Grant-in Aid for Scientific Research (No. 24710250) from the Japan Society for the Promotion of Science (JSPS).
発行日 2015-02-27
出版物タイトル The Journal of organic chemistry
80巻
6号
出版者 American Chemical Society
開始ページ 3111
終了ページ 3123
ISSN 00223263
NCID AA00704100
資料タイプ 学術雑誌論文
言語 English
OAI-PMH Set 岡山大学
論文のバージョン author
PubMed ID 25723589
DOI 10.1021/acs.joc.5b00027
Web of Sience KeyUT 000351558400017
関連URL isVersionOf https://doi.org/10.1021/acs.joc.5b00027
フルテキストURL Chemistry_22_6_1984.pdf
著者 Takamura, Hiroyoshi| Fujiwara, Takayuki| Kawakubo, Yohei| Kadota, Isao| Uemura, Daisuke|
抄録 We have synthesized eight possible diastereoisomers 3 a-h of the C79-C97 fragment of symbiodinolide (1) in a stereodivergent manner by utilizing a dithiane addition to the aldehyde as a key step. Comparison of the 13 C NMR chemical shifts of the natural product 1 and the synthetic products 3 a-h indicated that the relative stereostructure of this fragment in symbiodinolide (1) is that represented in 3 a or f. We have stereodivergently synthesized eight possible diastereoisomers of the C94-C104 fragment 4 a-h, and we have compared their 13 C NMR chemical shifts with those of the natural product, which established the relative stereochemistry of this fragment to be that described in diastereoisomers 4 a or e. By combining the stereostructural outcomes of the C79-C97 and C94-C104 fragments, we have proposed four candidate compounds of the C79-C104 fragment 2 a-d. We also synthesized diastereoisomers 2 a and b (2 a in the preceding article; Chem. Eur. J. 2015, DOI: 10.1002/chem.201503880) by a Julia-Kocienski olefination and diastereoisomers 2 c and d by a Wittig reaction. By comparing the 13 C NMR chemical shifts of natural symbiodinolide (1) with those of the synthetic products 2 a-d, we have reassigned the stereostructure of the C79-C104 fragment of natural product 1 to be that depicted in diastereoisomer 2 b.
キーワード macrocycles natural products polyols stereodivergent synthesis structure elucidation
備考 This is an article published by WILEY‐VCH We acknowledge JGC-S Scholarship Foundation, The Naito Foundation, The Sumitomo Foundation, and The Uehara Memorial Foundation for their financial supports. This research was supported by a Grant-in Aid for Scientific Research (No. 24710250) from the Japan Society for the Promotion of Science (JSPS).
発行日 2016-02
出版物タイトル Chemistry - A European Journal
22巻
6号
出版者 WILEY‐VCH
開始ページ 1984
終了ページ 1996
ISSN 0947-6539
NCID AA11076269
資料タイプ 学術雑誌論文
言語 English
OAI-PMH Set 岡山大学
著作権者 https://creativecommons.org/licenses/by-nc-nd/4.0/deed.ja
論文のバージョン author
PubMed ID 26742818
DOI 10.1002/chem.201503881
Web of Sience KeyUT 000368925200016
関連URL isVersionOf https://doi.org/10.1002/chem.201503881
フルテキストURL Chemistry_22_6_1979.pdf
著者 Takamura, Hiroyoshi| Fujiwara, Takayuki| Kawakubo, Yohei| Kadota, Isao| Uemura, Daisuke|
抄録 Stereoselective and streamlined synthesis of the proposed C79-C104 fragment 2 of symbiodinolide (1), a polyol marine natural product with a molecular weight of 2860, was achieved. In the synthetic route, the proposed C79-C104 fragment 2 was synthesized by utilizing a Julia-Kocienski olefination and subsequent Sharpless asymmetric dihydroxylation as key transformations in a convergent manner. Detailed comparison of the 13 C NMR chemical shifts between the natural product and the synthetic C79-C104 fragment 2 revealed that the stereostructure at the C91-C99 carbon chain moiety of symbiodinolide (1) should be reinvestigated.
キーワード macrocycles natural products polyols stereoselective synthesis structure elucidation
備考 This is an article published by Wiley-VCH We appreciate JGC-S Scholarship Foundation, The Naito Foundation, The Sumitomo Foundation, and The Uehara Memorial Foundation for their financial supports. This research was supported by a Grant-in Aid for Scientific Research (No. 24710250) from the Japan Society for the Promotion of Science (JSPS)
発行日 2016-02
出版物タイトル Chemistry - A European Journal
22巻
6号
出版者 Wiley-VCH
開始ページ 1979
終了ページ 1983
ISSN 0947-6539
NCID AA11076269
資料タイプ 学術雑誌論文
言語 English
OAI-PMH Set 岡山大学
著作権者 https://creativecommons.org/licenses/by-nc-nd/4.0/deed.ja
論文のバージョン author
PubMed ID 26661715
DOI 10.1002/chem.201503880
Web of Sience KeyUT 000368925200015
関連URL isVersionOf https://doi.org/10.1002/chem.201503880
フルテキストURL Org_Lett_18_9_2110.pdf
著者 Takamura, Hiroyoshi| Kikuchi, Takahiro| Endo, Noriyuki| Fukuda, Yuji| Kadota, Isao|
抄録 The first total syntheses of sarcophytonolide H and the originally proposed and correct structures of isosarcophytonolide D have been achieved via transannular ring-closing metathesis (RCM). These total syntheses culminated in the stereostructural confirmation of sarcophytonolide H and the reassignment of isosarcophytonolide D, respectively. The antifouling activity of the synthetic sarcophytonolide H and its analogues was also evaluated.
備考 This is an Accepted Manuscript of an article published by American Chemical Society This work was supported by Okayama Foundation for Science and Technology and JSPS KAKENHI (24710250).
発行日 2016-05-06
出版物タイトル Organic Letters
18巻
9号
出版者 American Chemical Society
開始ページ 2110
終了ページ 2113
ISSN 15237060
NCID AA11347843
資料タイプ 学術雑誌論文
言語 English
OAI-PMH Set 岡山大学
論文のバージョン author
PubMed ID 27093115
DOI 10.1021/acs.orglett.6b00737
Web of Sience KeyUT 000375891700042
関連URL isVersionOf https://doi.org/10.1021/acs.orglett.6b00737
フルテキストURL Org_Biomol_Chem_15_26_5549.pdf
著者 Takamura, Hiroyoshi| Ohashi, Takumi| Kikuchi, Takahiro| Endo, Noriyuki| Fukuda, Yuji| Kadota, Isao|
抄録 Hybrid molecules consisting of geraniol and butenolide were designed and synthesized by the late-stage divergent strategy. In the synthetic route, ring-closing metathesis was utilized for the construction of a butenolide moiety. A biological evaluation of the eight synthetic hybrid compounds revealed that these molecules exhibit antifouling activity against the cypris larvae of the barnacle Balanus (Amphibalanus) amphitrite with EC50 values of 0.30-1.31 μg mL-1. These results show that hybridization of the geraniol and butenolide structural motifs resulted in the enhancement of the antifouling activity.
備考 This is an Accepted Manuscript of an article published by Royal Society of Chemistry We are grateful to Okayama Foundation for Science and Technology and The Yakumo Foundation for Environmental Science for financial support.
発行日 2017-06-13
出版物タイトル Organic and Biomolecular Chemistry
15巻
26号
出版者 Royal Society of Chemistry
開始ページ 5549
終了ページ 5555
ISSN 14770520
NCID AA1168650X
資料タイプ 学術雑誌論文
言語 English
OAI-PMH Set 岡山大学
論文のバージョン author
PubMed ID 28632269
DOI 10.1039/c7ob01160a
Web of Sience KeyUT 000405003900014
関連URL isVersionOf https://doi.org/10.1039/c7ob01160a
フルテキストURL Chemistry_23_68_17191.pdf
著者 Takamura, Hiroyoshi| Katsube, Tomoya| Okamoto, Kazuki| Kadota, Isao|
抄録 The first total synthesis of two possible diastereomers of natural 6-chlorotetrahydrofuran acetogenin 1 has been achieved. The synthetic route features 5-exo-tet cyclization, Z selective Wittig reaction and Julia olefination for the construction of conjugated diene and enyne moieties, and stereoselective chlorination. Comparison of their 1 H and 13 C NMR data and specific rotation with those of the natural product elucidated the absolute configuration of natural (-)-6-chlorotetrahydrofuran acetogenin 1.
キーワード natural products stereoselective synthesis structure elucidation tetrahydrofuran total synthesis
備考 This is an article published by Wiley‐VCH
発行日 2017-12-06
出版物タイトル Chemistry - A European Journal
23巻
68号
出版者 Wiley‐VCH
開始ページ 17191
終了ページ 17194
ISSN 09476539
NCID AA11076269
資料タイプ 学術雑誌論文
言語 English
OAI-PMH Set 岡山大学
著作権者 https://creativecommons.org/licenses/by-nc-nd/4.0/deed.ja
論文のバージョン author
PubMed ID 29083058
DOI 10.1002/chem.201703234
Web of Sience KeyUT 000417508800005
関連URL isVersionOf https://doi.org/10.1002/chem.201703234
著者 Yoshimoto, Kaori| Takamura, Hiroyoshi| Kadota, Isao| 本瀬 宏康| Takahashi, Taku|
発行日 2016-02-16
出版物タイトル Scientific Reports
6巻
資料タイプ 学術雑誌論文
著者 Kadota, Isao| Abe, Takashi| Uni, Miyuki| Takamura, Hiroyoshi| Yamamoto, Yoshinori|
発行日 2008-06-19
出版物タイトル Tetrahedron Letters
49巻
資料タイプ 学術雑誌論文