130625-81-9Relevant articles and documents
Total Synthesis of the Mycotoxin (-)-Zearalenone based on Macrocyclisation using a Cinnamyl Radical Intermediate
Hitchcock, Stephen A.,Pattenden, Gerald
, p. 1323 - 1328 (2007/10/02)
A concise synthesis of optically active (-)-zearalenone, which uses a novel 14-endo-trig macrocyclisation from a cinnamyl radical intermediate onto an α,β-enone electrophore as a key feature, is described.
A Diastereoselective Synthesis of the Polyketide Antibiotic Citrinin using Toluate Anion Chemistry
Barber, Jill A.,Staunton, James,Wilkinson, Michael R.
, p. 2101 - 2110 (2007/10/02)
The diastereoselectivity of various synthetic approaches to (+/-)-threo-3-(3,5-dihydroxy-2-methylphenyl)butan-2-ol ('Phenol B') (4), based on reactions of benzyl anions with electrophiles, has been investigated.The anion (9) derived from ethyl 2,4-dimethoxy-6-ethylbenzoate reacted with acetaldehyde to give mainly an erythro-product isolated as the lactone (12); acetylation with acetyl chloride to give a ketone, followed by reduction, gave mainly the required threo-lactone (11).An alternative route was frustrated by decomposition of the benzyl anion derived from 3,4-dihydro-6,8-dimethoxy-3-methyl-1H-2-benzopyran-1-one (17).Reduction of the carbonyl group of the threo-lactone (11) to a methyl gave the dimethyl ether of 'Phenol B', which was converted into (+/-)-citrinin (1).