Strained cyclic allenes allow for the rapid construction of complex, bicyclic systems when trapped in Diels–Alder cycloadditions. We present enantiospecific and regio- and diastereoselective (4+2) cycloadditions of fleeting azacyclic allenes with pyrones. The asymmetric synthesis of chiral azacyclic allene precursors will be discussed, in addition to factors governing regioselectivity, diastereoselectivity, and enantiospecificity. Furthermore, the application of strained azacyclic allenes will be demonstrated in an enantiospecific manner toward the first total synthesis of (–)-lissodendoric acid A.

Leveraging chiral strained cyclic allenes in Diels–Alder cycloadditions toward the synthesis of (–)-lissodendoric acid A

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