916757-52-3

Upstream product

• 931416-77-2 2,2-dimethyl-5-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-vinyl]-benzo[1,3]dioxin-4-one 
• 41309-43-7 (2-bromovinyl)trimethylsilane 

Downstream Products

• 916757-59-0 2-(4-bromo-buta-1,3-dienyl)-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 
• 931416-87-4 2-(4-bromo-buta-1,3-dienyl)-6-triisopropylsilanyloxy-benzoic acid 3,7,9-tris-(tert-butyl-dimethyl-silanyloxy)-1-[2-(tert-butyl-dimethyl-silanyloxy)-propyl]-11-methyl-tetradeca-5,11,13-trienyl ester 
• 916757-58-9 2-acetoxy-6-(4-bromo-buta-1,3-dienyl)-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 
• 916757-45-4 2-acetoxy-6-(4-bromo-buta-1,3-dienyl)-benzoic acid 
• 916757-69-2 2-(4-bromo-buta-1,3-dienyl)-6-hydroxy-benzoic acid 

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).

Total synthesis of marinomycins A-C

(Chemical Equation Presented) Ocean's three: Unearthed from the bottom of the ocean off the coast of La Jolla (California, USA), marinomycins A-C, which differ in geometry about the C8-C9 and C8′-C9′ double bonds, have been prepared by total synthesis through a strategy that features a Suzuki coupling reaction to forge their remarkable polyunsaturated 44-membered-ring systems (see picture).