Synthesis of the C20–C32 Tetrahydropyran Core of the Phorboxazoles and the C22 Epimer via a Stereodivergent Michael Reaction
✍ Scribed by Clarke, Paul A.; Ermanis, Kristaps
- Book ID
- 120372556
- Publisher
- American Chemical Society
- Year
- 2012
- Tongue
- English
- Weight
- 369 KB
- Volume
- 14
- Category
- Article
- ISSN
- 1523-7060
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Studies on the synthesis of the anticancer natural products, the phorboxazoles, have led to the synthesis of the C21-C32 penta-substituted tetrahydropyran core which is epimeric to the natural product at C23. The synthesis was achieved in only seven linear steps. The key steps were the use of a Masa
A stereocontrolled synthesis of two fragments comprising the macrocyclic core of Phorboxazole A is described. The C3-C19 bis-pyran segment is prepared utilizing reiterative enantioselective allylations from homochiral aUylstannanes followed by stereoselective cyclizations. The pentasubstituted tetra