Synthesis of the northern hemisphere of the milbemycins using a new strategy for the formation of the C15 to C16 bond.
✍ Scribed by David Culshaw; Peter Grice; Steven V. Ley; Gary A. Strange
- Book ID
- 104229092
- Publisher
- Elsevier Science
- Year
- 1985
- Tongue
- French
- Weight
- 143 KB
- Volume
- 26
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
Using a new convergent route the synthesis of the C-11 to C-25 northern hemisphere fragment of the milbemycins has been achieved.
📜 SIMILAR VOLUMES
A stereospecific synthesis of a potential Cl&Cl9 fragment of the novel antineoplastic macrolide amphidinolide-A is described. ## Amphidinolide-A (1) was isolated from dinoflagellate Amphidinium sp. by Kobayashi et. all. This compound has shown in v&-u activity against L1210 (I&j0 2.4 ng/mL) murin
Upon photooxygenation in the presence of base, a-oximinocarbonyl compounds undergo clean oxidative C C cleavage giving rise to mixtures of esters and acids. The mechanism of these reactions involves some unusual peroxidic intermediates, including a 2,3,5-trioxapentanes.
Addition of carbon radicals generated from organoselenium reagents P SeR: R= COPh, CO\*Et, CH,CO,Et, CH2COMe, and CH,CN) to 4',5'-unsaturated uraciinucleosides was found to provide a highly efficient entry to C-C bond formation at the 5'-position, the stereochemical outcome of which is dependent upo
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.