Abstract
The synthesis of vallartanone B, a γ-pyrone-containing polypoprionate from the marine mollusc Siphonaria maura, is described. A γ-pyrone moiety, which was constructed by PPh 3 -CCl 4 cyclization of a β-triketone, and a C1-C6 segment were joined by a Sn(OTf) 2 aldol reaction and converted to vallartanone B. This synthesis allows for revision of the stereochemistry at C8. A conformational analysis was performed using PM3 to examine the proposed interpretation of its CD spectrum.
| Original language | English |
|---|---|
| Pages (from-to) | 13901-13908 |
| Number of pages | 8 |
| Journal | Tetrahedron |
| Volume | 52 |
| Issue number | 44 |
| DOIs | |
| Publication status | Published - 1996 Oct 28 |
| Externally published | Yes |
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
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Arimoto, H., Yokoyama, R., Nakamura, K., Okumura, Y., & Uemura, D. (1996). Vallartanone B: Synthesis and related studies. Tetrahedron, 52(44), 13901-13908. https://doi.org/10.1016/0040-4020(96)00852-6