Abstract
Tetrahydropyrans are common motifs in natural products and have now been constructed with high stereocontrol through a three‐component allylboration‐Prins reaction sequence. This methodology has been applied to a concise (13 steps) and efficient (14 % overall yield) synthesis of the macrolide (−)‐clavosolide A. The synthesis also features an early stage glycosidation reaction to introduce the xylose moiety and a lithiation‐borylation reaction to attach the cyclopropyl‐containing side chain.
Highlights
Creating increasingly efficient syntheses of common structural motifs found in Nature is a long-running objective in organic synthesis
This molecule has been prepared by a variety of strategies and the tetrasubstituted tetrahydropyran (THP) core alone has been constructed in ! 6 steps.[3]
In this paper we report our success in developing the three-component allylboration–Prins reaction for the rapid stereocontrolled assembly of substituted THPs and in developing further improvements to our lithiation–borylation protocol and addressing other issues of stereocontrol so that every step in our short synthesis is highly stereoselective (> 95:5 dr)
Summary
Creating increasingly efficient syntheses of common structural motifs found in Nature is a long-running objective in organic synthesis. Lithiation–borylation[4] has emerged as a powerful tool for the synthesis of chiral boronic esters including allylic boronic esters.[5] We reasoned that this methodology, in combination with our improved allylboration of aldehydes[6] followed directly by a Prins cyclisation[7,8] could lead to a short, and highly stereoselective synthesis of the THP core of (À)clavosolide A in just three steps.
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