Asymmetric Total Syntheses of Two Possible Diastereomers of Gliomasolide E and Its Structural Elucidation

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–...

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Bibliographic Details
Published in:Journal of organic chemistry 2017-01, Vol.82 (2), p.1053-1063
Main Authors: Reddy, Ramidi Gopal, Venkateshwarlu, Ravula, Ramakrishna, Kallaganti V. S, Yadav, Jhillu S, Mohapatra, Debendra K
Format: Article
Language:English
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Summary: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 1H and 13C 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).
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b02611