2026-10-13T13:16:50Z
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2026-09-29T22:09:10Z
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Convergent Synthesis
of a Desmethyl Analogue of Amycomycin
Max Schòˆnenbroicher (9917005)
Florian Heppner (23122687)
Maximilian Seul (9917008)
Simon Morgenschweis (23122684)
Dirk Menche (1426639)
Biochemistry
Space Science
Microbiology
Chemical Sciences not elsewhere classified
Sociology
Information Systems not elsewhere classified
Computational Biology
advanced substrates due
acyl tetramic acid
revised coupling strategy
>- acyl transfer
convergent strategy
wittig olefination
steric hindrance
efficient assembly
desmethyl analogue
convergent synthesis
complex 3
complete skeleton
central challenge
The convergent synthesis of a desmethyl analogue of amycomycin,
the aglycon of vancoresmycin, is presented. The central challenge
of the convergent strategy was an initial aldol condensation approach,
which failed on advanced substrates due to steric hindrance, prompting
a revised coupling strategy. The successful route employed nucleophilic
vinyl addition, complemented by a Boron-Wittig olefination to construct
sterically congested vinyl boronates. A late-stage <i>O</i>- to <i>C</i>-acyl transfer on a complex 3-acyl tetramic
acid was essential for the efficient assembly of the complete skeleton
of desmethyl amycomycin.
2026-09-29T00:00:00Z
Text
Journal contribution
10.1021/acs.joc.6c01817.s001
https://figshare.com/articles/journal_contribution/Convergent_Synthesis_of_a_Desmethyl_Analogue_of_Amycomycin/34028080
CC BY-NC 4.0