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