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Studies in marine macrolide synthesis: Synthesis of a C16C28 subunit of spongistatin 1 (altohyrtin A) incorporating the CD-spiroacetal moiety

✍ Scribed by Ian Paterson; Debra J Wallace; Karl R Gibson

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
270 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

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.

📜 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.