Abstract
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 13C 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.
Original language | English |
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Pages (from-to) | 1979-1983 |
Number of pages | 5 |
Journal | Chemistry - A European Journal |
Volume | 22 |
Issue number | 6 |
DOIs | |
Publication status | Published - Feb 5 2016 |
Keywords
- macrocycles
- natural products
- polyols
- stereoselective synthesis
- structure elucidation
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
- Organic Chemistry