Asymmetric Total Syntheses of Two Possible Diastereomers of Gliomasolide E and Its Structural Elucidation
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- 作者：Ramidi Gopal Reddy ; Ravula Venkateshwarlu ; Kallaganti V. S. Ramakrishna ; Jhillu S. Yadav ; Debendra K. Mohapatra
- 刊名：Journal of Organic Chemistry
- 出版年：2017
- 出版时间：January 20, 2017
- 年：2017
- 卷：82
- 期：2
- 页码：1053-1063
- 全文大小：574K
- ISSN：1520-6904
文摘
The first total syntheses of two possible diastereomers of gliomasolide E, a 14-membered macrolides isolated from the marine sponge Phakellia fusca Thiele, which was collected from the South China Sea, is reported. Highlights of the synthesis include macrolactonization through intramolecular Horner–Wadsworth–Emmons olefination, Yamaguchi–Hirao alkynylation, and base-induced elimination reactions for propargyl alcohol synthesis as the key reactions. Detailed comparison of their p>1 p>H and p>13 p>C NMR (1D and 2D NMR data) and specific rotation with those of the natural product revealed that the absolute stereochemistry of gliomasolide E should be (2E,5R,7R,9R,13R).