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 |
|---|---|
| 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
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Cite this
Takamura, H., Fujiwara, T., Kawakubo, Y., Kadota, I., & Uemura, D. (2016). Stereoselective Synthesis of the Proposed C79-C104 Fragment of Symbiodinolide. Chemistry - A European Journal, 22(6), 1979-1983. https://doi.org/10.1002/chem.201503880