In addi on to the mechanis c inves ga ons, several other experiments were conducted. First, an a empt was made to replace iodine with another electrophilic oxidizing agent, bromine, in the reac on with both exo,exo and exo,endo diastereomers 2. However, in both cases, only an epimerized mixture of diesters 2 was isolated, and the desired product was not detected even in trace amounts. These findings prompted further considera on of the radical nature of the cycliza on process . Literature reports a precedent for the assembly of the stellane core through intramolecular biradical recombina on, as observed when diketone 3 was treated with SmI2, resul ng in the forma on of stellane 1,5-diole . Inspired by this, we a empted a similar cycliza on from diesters 2 by genera ng the corresponding radical intermediates through Mn(OAc)3-based oxida on .