Figure Example for different phloroglucinol meroterpenoids with various biological activities. Scheme 1 Biosynthesis of cleistocaltone A (1) proposed by Ye, Wang, and coworkers and retrosynthetic analysis both featuring an IMDA as the key step. This reaction forges the characteristic 10-membe r e d macrocycle found in 7 (Scheme 1). Ye, Wang, and coworke r s succeeded in isolating 24 mg of (±)-cleistocaltone A (1) from 15 kg of plant material, highlighting the scarcity of this compou n d from biological sources. This underlines the significance of chemical synthesis to produce substantial quantities of (±)cleistocaltone A (1) for further biological evaluation. In recent years, biomimetic strategies have emerged as an intriguing and efficient approach for synthesizing comple x natural products. These strategies elegantly mimic the pathways found in nature. By harnessing the innat e reactivity of molecules, biomimetic syntheses often minimize the need for protection groups, resulting in greater efficienc y and sustainability. Mirroring the proposed biosynthetic pathway, we envision e d an IMDA as the pivotal step for constructing the 10-membe r e d macrocycle of 8. To generate the diene moiety in 9 for the IMDA, we planned a selective desaturation at the terminus of the geranyl group in 6, obtained from geranyl acetate (10). Thi s geranyl unit would be attached to the nucleophilic carbon ato m of methylated phloroglucinol 11 using a Tsuji-Trost alkylation. The phloroglucinol building block would be synthesized fro m commercially available 2-acetyl phloroglucinol (12) throu gh trimethylation and an aldol condensation.