Regiocontrolled cleavage of the isocembrol cycle at the Δ2 bond and its transformation into 15-membered macrolide

Isocembrol C(3)-ketoxime was synthesized regioselectively and the C—C bond was cleaved under the standard Beckmann fragmentation conditions. Subsequent hydrolysis of nitrile to give ω-hydroxy acid and cyclization on treatment with 2,2′-dipyridyl disulfide finalized the synthesis of 15-membered macro...

Full description

Saved in:
Bibliographic Details
Published in:Russian chemical bulletin 2023-10, Vol.72 (10), p.2466-2472
Main Authors: Salikhov, Sh. M., Faizullina, L. Kh, Valeev, F. A.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Full Articles
Hydroxy acids
Inorganic Chemistry
Organic Chemistry
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Isocembrol C(3)-ketoxime was synthesized regioselectively and the C—C bond was cleaved under the standard Beckmann fragmentation conditions. Subsequent hydrolysis of nitrile to give ω-hydroxy acid and cyclization on treatment with 2,2′-dipyridyl disulfide finalized the synthesis of 15-membered macrolide.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-023-4048-y