Abstract
The transformation of a common synthetic intermediate of aspergillides B and C into aspergillide A, a cytotoxin produced by a marine-derived fungus, has been accomplished in an eleven-step sequence involving an efficient proline-catalyzed isomerization of a 2,6-trans-substituted tetrahydropyran-2- acetaldehyde intermediate into the corresponding cis isomer and the Yamaguchi macrolactonization as the key steps.
Original language | English |
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Pages (from-to) | 2882-2888 |
Number of pages | 7 |
Journal | Tetrahedron |
Volume | 67 |
Issue number | 16 |
DOIs | |
Publication status | Published - 2011 Apr 22 |
Keywords
- Aspergillide
- Cytotoxic
- Isomerization
- Macrolide
- Total synthesis
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry