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This article discusses the progress made in the enantioselective total synthesis of γ-rubromycin, a Streptomyces antibiotic. The researchers previously reported a successful photoirradiation method using a chiral, non-racemic 1,2-naphthoquinone to produce an enantioenriched spiroacetal. However, in their latest study, they found that the viability of the photochemical reaction depended on the chromophore structure of the quinones. They also observed that the color of the quinones correlated with their reactivity, with yellow or orange quinones being reactive and red or dark red-purple quinones being unreactive. Further studies are being conducted to gain insights into the photoreaction viability and guide substrate design for the synthesis of γ-rubromycin. [Extracted from the article]