Abstract
An enantio- and diastereoselective synthesis of the C17–C29 fragment of amphidinolide N, an extremely potent macrocyclic cytotoxin of marine origin, has been accomplished from a known olefinic ester by a 10-step sequence that involves a ring opening of a chiral epoxide with a dithiane derivative to construct the full carbon skeleton, a highly diastereoselective reduction of a β-hydroxy ketone intermediate to install the C21 asymmetric center, and a one-pot Sharpless AD/cyclization sequence to form a trans-substituted tetrahydrofuran ring system.
| Original language | English |
|---|---|
| Pages (from-to) | 5240-5242 |
| Number of pages | 3 |
| Journal | Tetrahedron Letters |
| Volume | 57 |
| Issue number | 47 |
| DOIs | |
| Publication status | Published - 2016 Jan 1 |
Keywords
- Amphidinolide
- Cytotoxic
- Macrolide
- Partial synthesis
- Polyketide
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
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Cite this
Fujishima, Y., Ogura, Y., Towada, R., Enomoto, M., & Kuwahara, S. (2016). Stereoselective synthesis of the C17–C29 fragment of amphidinolide N. Tetrahedron Letters, 57(47), 5240-5242. https://doi.org/10.1016/j.tetlet.2016.10.038