- Total synthesis of (±)-, (-)-, and (+)-oudemansin X
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Three kinds of oudemansin X, (-)-1, (+)-1 and (±)-1, were totally synthesized. The key point in the present chiral synthesis was the enantioselective acetylation of the racemic alcohols, (±)-5 and (±)-8, using lipase in an organic solvent. The synthetic (-)-1 was found to exhibit strong antifungal activity against several molds and yeasts.
- Umezawa,Nozawa,Nagumo,Akita
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p. 1111 - 1118
(2007/10/02)
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- Total synthesis of (-)-oudemansin X based on enzymatic resolution using immobilized lipase
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(-)-Oudemansin X (1) was synthesized based on enzymatic resolution of (±)-diol 5 using immobilized lipase.
- Akita,Umezawa,Nozawa,Nagumo
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p. 757 - 760
(2007/10/02)
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- Synthesis of Methyl 5-Aryl-3-oxo-4-pentenoates and Novel Substituted Cyclopentenones
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The cinnamoyl- (1a-j) and (5-phenyl-2,4-pentadienoyl)- (1k) ketene dithioacetals are shown to undergo methanolysis in the presence of ether-boron trifluoride complex and mercury(II) chloride to the corresponding methyl 5-aryl-3-oxo-4-pentenoates 2a-j and 3-oxo-7-phenyl-4,6-heptadienoate (2k), respectively, in good yields.However, the corresponding (2-methylcinnamoyl)ketene dithioacetals 3a-f, under identical reaction conditions, undergo Nazarov cyclization to give the corresponding substituted cyclopentenones 4a-f.
- Asokan, C. V.,Bhattacharji, S.,Ila, H.,Junjappa, H.
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p. 281 - 283
(2007/10/02)
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