Studies in marine macrolide synthesis: stereocontrolled synthesis of a C21–C34 subunit of the aplyronines
✍ Scribed by Ian Paterson; Simon B Blakey; Cameron J Cowden
- Publisher
- Elsevier Science
- Year
- 2002
- Tongue
- French
- Weight
- 129 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
📜 SIMILAR VOLUMES
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
The C36-C46 subunit 3, containing the F ring of spongistatin 1 (1), was prepared in 12 steps from ketone (R)-7. Key steps include: (i) the boron-mediated anti aldol reaction, 7 9; (ii) the Sharpless AD, 6 --~ 13; and (iii) an intramolecular hetero-Michael addition, followed by base-promoted equilibr