title: Truncated borrelidin analogues: synthesis by sequential cross metathesis/olefination for the southern fragment and biological evaluation.
abstract: 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.
authors: Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany. sabine.laschat@oc.uni-stuttgart.de.
authors: Tülay
authors: T
authors: Gündemir-Durmaz
authors: Fabian
authors: F
authors: Schmid
authors: Yana
authors: Y
authors: El Baz
authors: Annette
authors: A
authors: Häusser
authors: Carmen
authors: C
authors: Schneider
authors: Ursula
authors: U
authors: Bilitewski
authors: Guntram
authors: G
authors: Rauhut
authors: Delphine
authors: D
authors: Garnier
authors: Angelika
authors: A
authors: Baro
authors: Sabine
authors: S
authors: Laschat
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry*; D000818:Animals; D002460:Cell Line; D002470:Cell Survival; D003500:Cyclization; D005233:Fatty Alcohols / Q000138:chemical synthesis / Q000494:pharmacology; D005347:Fibroblasts / Q000166:cytology / Q000187:drug effects; D006801:Humans; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000494:pharmacology*; D051379:Mice; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011789:Quantum Theory; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000498:Allyl Compounds; D005233:Fatty Alcohols; D047028:Macrocyclic Compounds; C005066:borrelidin