Asterriquinone B1 (1) and its de-methyl analog, demethylasterriquinone B1 (2), which are members of a group of bis-indolyl benzoquinones, were isolated from strains of Aspergillus terreus and Pseudomassaria sp., respectively. Especially, the latter product 2 has been reported by Merck group to be the novel insulin receptor activator, that mimics the function of insulin, and therefore, is of potential therapeutic interest for the treatment of diabetes. The total synthesis of the natural products 1 and 2 has been also accomplished by Merck group using elegant strategies with the rearrangement of pyrandione. We describe herein a short and convergent synthesis of asterriquinone B1 (1) and demethylasterriquinone B1 (2). The construction of 1 and 2 entailed the synthesis of three building blocks, the substituted indols 3 and 5 and the dibromoquinone 4. Compounds 3 and 4 were prepared from 2-iodoaniline (6) and 2,5-dimethoxy-1,4-quinone (7) by the reported processes. The C2 substituted indol 5 was synthesized by chlorination of indol (8) with NCS to give 3-chloroindol (9), followed by treatment of prenyl-9-BBN. Reaction of 4 with the lithiated 5 gave selectively the mono-substituted 10 without substitution of the bromide in 61% yield, which seemed to proceed in the Michael-retro Michael type based on the stability of the produced anion between the carbonyl and bromo groups. Another indol moiety was further introduced onto 10 by using the lithiated 3 to afford the disubstituted 11 in 72% yield. A solution of 11 in a mixture of dioxane and aq KOH solution was refluxed for 2 hours, after neutralization and filtration, the filtrates were evaporated and chromatographed to give purple solids of 2 (30% yield) and 12 (18% yield). The synthetic product 2 was identical in all respects with natural demethylasterriquinone B1. Alternatively, 2 was obtained from asterriquinone B1 (1) by de-O-methylation with aq KOH in EtOH in 78% yield. Asterriquinone B1 (1) was synthesized in 74% yield from 11 by treatment with NaOH in MeOH for 4 hours, which was identical in all respects with the natural product. At the heart of the synthesis described herein is the selective introduction of two different components 3 and 5 onto the benzoquinone core 4.