Organic and Biomolecular Chemistry p. 8261 - 8269 (2016)
Update date:2022-09-26
Topics:
Gündemir-Durmaz, Tülay
Schmid, Fabian
El Baz, Yana
H?usser, Annette
Schneider, Carmen
Bilitewski, Ursula
Rauhut, Guntram
Garnier, Delphine
Baro, Angelika
Laschat, Sabine
The construction of novel borrelidin analogues is reported in which the northern fragment is truncated to a simple hydroxyundecanecarboxylate and the original cyclopentanecarboxylic acid in the southern fragment is replaced with different six-membered rings. The required precursors were prepared by cross metathesis of the appropriate carbocycle-based homoallylic alcohol with crotonaldehyde followed by HWE olefination of the resulting enal with bromocyanophosphonate. The key aldehyde for intramolecular cross coupling was accessible by oxidation of the hydroxy group of the linked undecanecarboxylate unit. Grignard mediated macrocyclization finally yielded the borrelidin related products. The investigation is complemented by SAR studies and quantum-chemical calculations.
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