Total Synthesis of Skipped Diene Natural Products

Skipped dienes (1,4-dienes) are widely distributed in a variety of biologically active natural products. The synthesis of these skipped dienes is a relatively undeveloped area compared with that of conjugated dienes (1,3-dienes) due to the sp(3)-hybridized carbon between two olefins. Especially, development of methods to meet both high stereoselectivity and convergency is highly challenging. This review focuses on recent advances in the synthesis of skipped dienes in the total synthesis of complex natural products, which are classified into three classes; a) skipped dienes comprised of two disubstituted olefins, b) skipped dienes including trisubstituted olefin(s), and c) 3-methyl skipped dienes.

Automated summary

Skipped dienes, found in various biologically active natural products, have relatively undeveloped synthesis methods compared to conjugated dienes due to challenges posed by the sp(3)-hybridized carbon between two olefins. Recent advances in the synthesis of skipped dienes for total synthesis of complex natural products are classified into three categories, focusing on methods to achieve both high stereoselectivity and convergency.