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Studies in biomimetic polyether synthesis: Synthesis of an A-ring subunit of etheromycin

โœ Scribed by Ian Paterson; Richard D. Tillyer; Glen R. Ryan

Publisher
Elsevier Science
Year
1993
Tongue
French
Weight
333 KB
Volume
34
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

The g-hydroxyketones 7.20, and 22 were prepared by stemocomrolled aldol reactions of (S)-and (N-18 with the enal 8. Acetmide hydrolysis gave the bicyclic acetals 23-2g, while tbe benxoate 26 gave the tetmhydropyran 6, corresponding to an A-ring subunit for 2-epi~mycin.

๐Ÿ“œ SIMILAR VOLUMES

Studies in marine macrolide synthesis: S
Studies in marine macrolide synthesis: Stereocontrolled synthesis of the F-ring subunit of spongistatin 1 (altohyrtin A)
โœ Ian Paterson; Linda E Keown ๐Ÿ“‚ Article ๐Ÿ“… 1997 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 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