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Studies in marine macrolide synthesis: Stereocontrolled synthesis of the AB-spiroacetal subunit of spongistatin 1 (altohyrtin A)

โœ Scribed by Ian Paterson; Renata M. Oballa; Roger D. Norcross


Publisher
Elsevier Science
Year
1996
Tongue
French
Weight
247 KB
Volume
37
Category
Article
ISSN
0040-4039

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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

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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.