Total asymmetric synthesis of a new 9,12-anhydroerythronolide aglycone
Two novel, potentially antimicrobial erythronolide aglycon analogs ((-)-9 and (-)-30, respectively), which incorporate a large number of contiguous stereogenic centers, have been prepared by multistep synthesis from simple chirons. The chemistry presented demonstrates the power of the so-called 'naked sugars of the second acneration' approach. As for the sporeamicins, our macrolides are 9,12-anhydroerythronotides, yet presenting a higher degree of complexity due to additional functional groups.
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Keywords: erythronolide-a ; stereocontrolled synthesis ; natural-products ; aldolreactions ; long-chain ; seco-acid ; (c5-c9)+(c3-c4)+(c1-c2)+(c11-c-13)sequence ; macrolide synthesis ; erythromycin ; derivatives
Record created on 2005-11-09, modified on 2016-08-08