(+)-Calanolide A was the first natural product identified as an active agent against HIV-1 and Mycobacterium tuberculosis(Mtb).In devising a scaffold-hopping strategy of structure modification of (+)-calanolide A,we focused on the synthesis of calanolides by replacing ring D with various five or six membered nitrogen-containing heterocycles,hoping to get further understanding of the structure-activity relationship. (+) - Calanolide A was the first natural product identified as an active agent against HIV-1 and Mycobacterium tuberculosis (Mtb). In devising a scaffold-hopping strategy of structure modification of (+) - calanolide A, we focused on the synthesis of calanolides by replacing ring D with various five or six membered nitrogen-containing heterocycles, hoping to get further understanding of the structure-activity relationship.