Synthesis of a C(1)-C(14)-containing fragment of callipeltoside A.
[formula: see text] A C(1)-C(14)-containing fragment of callipeltoside A (1, Scheme 1) was synthesized efficiently via a dianion aldol coupling reaction between aldehyde 2 and ketoester 3. A surprising lack of reactivity between the alkenes in 13 and the Grubbs initiator 15 was encountered. An equally surprising rate acceleration of the reaction between 15 and allylic alcohols (alk-1-en-3-ols) as well as their subsequent cleavage to methyl ketones was discovered. In situ 1H NMR analysis has proven to be a very useful tool for monitoring RCM reactions of complex substrates such as 13.
Hoye
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Department of Chemistry, University of Minnesota, Minneapolis 55455, USA. hoye@chem.umn.edu
Zhao
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D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D000903:Antibiotics, Antineoplastic / Q000737:chemistry*; D018942:Macrolides; D009682:Magnetic Resonance Spectroscopy; D010446:Peptide Fragments / Q000138:chemical synthesis / Q000737:chemistry; D011161:Porifera / Q000737:chemistry*
D000900:Anti-Bacterial Agents; D000903:Antibiotics, Antineoplastic; D018942:Macrolides; D010446:Peptide Fragments; C410329:callipeltoside A