Enantioselective Synthesis of a C1-C9 Moiety of Tylonolide, Tylosin Aglycon
- 1 October 1998
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1998 (10) , 1135-1137
- https://doi.org/10.1055/s-1998-1873
Abstract
In an approach to the C1-C9 eastern part 2 of tylonolide, aglycon of tylosin 1, an extension of the Hoppe reaction was, in a first key step, carried out between carbamate 6 and optically active aldehyde 5a and γ-lactol 5b. The latter gave the expected 7b adduct in 85% yield. After a homologation sequence, the C1-C7 fragment 14b was prepared and submitted to a second allylation reaction with crotyl N,N-diisopropyl carbamate to deliver compound 16 in 80% yield as a C1-C9 moiety of tylonolide.Keywords
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