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Studies in marine macrolide synthesis: Synthesis of the C1C15 subunit of spongistatin 1 (altohyrtin A) and 15,16-anti aldol coupling reactions

✍ Scribed by Ian Paterson; Renata M. Oballa

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

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✦ Synopsis

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.

📜 SIMILAR VOLUMES

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.

Studies in marine macrolide synthesis: S
Studies in marine macrolide synthesis: Stereocontrolled synthesis of the F-ring subunit of spongistatin 1 (altohyrtin A)
✍ Ian Paterson; Linda E Keown 📂 Article 📅 1997 🏛 Elsevier Science 🌐 French ⚖ 237 KB

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