Synthesis of optically pure (+)-puraquinonic acid and assignment of absolute configuration to natural (-)-puraquinonic acid. Use of radical cyclization for asymmetric …
DLJ Clive, M Yu, M Sannigrahi
Index: Clive, Derrick L. J.; Yu, Maolin; Sannigrahi, Mousumi Journal of Organic Chemistry, 2004 , vol. 69, # 12 p. 4116 - 4125
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Citation Number: 19
Abstract
An asymmetric aldol reaction between aldehyde 31 and imide 32, followed at a later stage by ring-closing metathesis (38→ 40), are key reactions used to make optically pure allylic alcohol 40. Radical cyclization of the derived Stork bromo acetals gives lactol ethers 43, which were degraded to generate a quaternary center carrying a methoxycarboxyl group (44→ 47). Compound 47 was converted into (+)-puraquinonic acid; and comparison with ...
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