938176-09-1

Upstream product

• 164014-59-9 5-ethynyl-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one 
• 931416-88-5 2,2-dimethyl-5-(2-triethylsilanyl-vinyl)-benzo[1,3]dioxin-4-one 
• 931416-89-6 5-(2-bromo-vinyl)-2,2-dimethyl-benzo[1,3]dioxin-4-one 

Downstream Products

• 931416-90-9 2-acetoxy-6-(2-bromo-vinyl)-benzoic acid 
• 931416-84-1 2-(2-bromo-vinyl)-6-triisopropylsilanyloxy-benzoic acid 3,7,9-tris-(tert-butyl-dimethyl-silanyloxy)-1-[2-(tert-butyl-dimethyl-silanyloxy)-propyl]-11-methyl-tetradeca-5,11-dien-13-ynyl ester 

Relevant academic research and scientific papers

Total synthesis of marinomycins A-C and of their monomeric counterparts monomarinomycin A and iso-monomarinomycin A

Marinomycins A-C (1-3), and their monomeric analogues monomarinomycin A (m-1) and iso-monomarinomycin A (m-2), were synthesized by a convergent strategy from key building blocks ketophosphonate 5, aldehyde 6, and dienyl bromide carboxylic acid 7. The first attempt to construct marinomycin A [1, convertible to marinomycins B (2) and C (3) by light] by direct Suzuki-type dimerization/ cyclization of boronic acid dienyl bromide 4 led to premature ring closure to afford, after global desilylation, monomarinomycin A (m-1) and iso-monomarinomycin A (m-2) in good yield and only small amounts (≤2%) of the desired product. A subsequent stepwise approach based on Suzuki-type couplings improved considerably the overall yield of marinomycin A (1), and hence of marinomycins B (2) and C (3). Alternative direct dimerization approaches based on the Stille and Heck coupling reactions also led to monomarinomycins A (m-1 and m-2), but failed to deliver useful amounts of marinomycin A (1).