𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Studies in marine macrolide synthesis: Stereocontrolled synthesis of the C1C11 and C15C27 subunits of aplyronine A

✍ Scribed by Ian Paterson; Cameron J Cowden; Michael D Woodrow

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
231 KB
Volume
39
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

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 ketone (S)-14 using a tin(ll)-mediated sa'n aldol reaction and CBS enone reduction,

📜 SIMILAR VOLUMES

Studies in marine macrolide synthesis: S
Studies in marine macrolide synthesis: Synthesis of the C1C15 subunit of spongistatin 1 (altohyrtin A) and 15,16-anti aldol coupling reactions
✍ Ian Paterson; Renata M. Oballa 📂 Article 📅 1997 🏛 Elsevier Science 🌐 French ⚖ 260 KB

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.

Studies in marine macrolide synthesis: S
Studies in marine macrolide synthesis: Synthesis of a C16C28 subunit of spongistatin 1 (altohyrtin A) incorporating the CD-spiroacetal moiety
✍ Ian Paterson; Debra J Wallace; Karl R Gibson 📂 Article 📅 1997 🏛 Elsevier Science 🌐 French ⚖ 270 KB

The C! 6-C28 ketone 3, containing the CD-spiroacetal of spongistatin 1 (1), was prepared in 17 steps from aldehyde 9. Both thermodynamic and kinetic conditions were explored for controlling the CD-acetal configuration.