Advances in the vinylogous Mukaiyama aldol reaction and its application to the synthesis of the C1C7 subunit of oleandolide
✍ Scribed by Jorma Hassfeld; Markus Kalesse
- Publisher
- Elsevier Science
- Year
- 2002
- Tongue
- French
- Weight
- 106 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The synthesis of a stereo pentade of the macrolide antibiotic oleandolide is reported. The C1 C7 fragment resembles the analogous segment of Panek's total synthesis of oleandolide. The use of the vinylogous Mukaiyama aldol reaction shortens the route significantly and has the advantage of utilizing an easily accessible ketene acetal.
📜 SIMILAR VOLUMES
The CI-C15 aldehyde 3, containing the AB-spiroacetal of spongistatin 1 (1), was prepared in 17 steps from methyl ketone (S)-8. The C15 and CI6 stereocentres could be introduced together, relying on Felkin-Anh control, by using a boron-mediated, anti aldol coupling reaction, as in 22 ~ 25 and 26.
The aplyronine C I-CII subunit 4, containing 4 stereocentres and the (E,E)-diene system, was prepared in 7 steps from ethyl ketone (R)-8 using a boron-mediated anti aldol reaction. The corresponding C 15-C27 subunit 5, containing 6 stereogenic centres and an (E)-alkene, was obtained in 10 steps from