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Studies in macrolide synthesis: A stereocontrolled synthesis of a (9S)-macrolide intermediate for oleandomycin using chiral boron reagents.

โœ Scribed by Ian Paterson; M.Anne Lister; Roger D. Norcross

Publisher
Elsevier Science
Year
1992
Tongue
French
Weight
350 KB
Volume
33
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

The (9s)-macrolide 1 (P = TBS) was prepared in 14 steps (5% yield) with 63% overall ds starting from the ethyl ketone ($2. The Cl-C7 and Q-C13 segments, 3 and 4, were obtained via boron enolate aldol reactions mediated by (+)-and (-)-(Ipc)zBOTf, respectively.

Conventional reduction conditions using Li in NHj/THF at -78 "C led to accompanying TBS migration to the Cl3 hydroxyl.

๐Ÿ“œ SIMILAR VOLUMES

Studies in macrolide synthesis: Stereoco
Studies in macrolide synthesis: Stereocontrolled synthesis of a C1๎—ธC13 segment of concanamycin A
โœ Ian Paterson; Malcolm D. McLeod ๐Ÿ“‚ Article ๐Ÿ“… 1997 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 329 KB

The Ct-Ct3 segment 6 of concanamycin A (1) was prepared by a highly stereocontrolled route (87% overall ds) in 16 steps from the ester 9. Key steps are the one-pot aldol/reduction, 8 + 12, and the HWB reaction, 18 + 19 + 6.8 1997 Elsevier Science Ltd.