175552-85-9

Upstream product

• 97330-03-5 (2E,4E)-5-Cyclohexyl-penta-2,4-dienoic acid 
• 2043-61-0 cyclohexanecarbaldehyde 
• 244024-09-7 C₂₀H₃₈O₃Si 
• 244024-04-2 triisopropylsilyl 5-ccyclohexylpenta-2E,4E-dienoate 

Downstream Products

• 182158-26-5 (2E,4E)-5-Cyclohexyl-penta-2,4-dienoic acid (2,2-dimethoxy-5-oxo-7-oxa-bicyclo[4.1.0]hept-3-en-3-yl)-amide 
• 321528-62-5 (2E,4E)-5-Cyclohexyl-penta-2,4-dienoic acid (6,6-dimethoxy-3-oxo-cyclohexa-1,4-dienyl)-amide 
• 208706-21-2 2-(5-cyclohexylpenta-2'E,4'E-dienoylamino)-1,4-benzoquinone 
• 175673-54-8 (2E,4E)-5-Cyclohexyl-penta-2,4-dienoic acid (2,5-dioxo-7-oxa-bicyclo[4.1.0]hept-3-en-3-yl)-amide 
• 211997-74-9 (2E,4E)-5-Cyclohexyl-penta-2,4-dienoic acid ((1R,6S)-2,2-dimethoxy-5-oxo-7-oxa-bicyclo[4.1.0]hept-3-en-3-yl)-amide 

Relevant academic research and scientific papers

Total synthesis of (±)-nisamycin

We have developed a highly convergent synthesis of the manumycin-type m- C7N-antibiotic nisamycin that is applicable to other members of this family of antibiotics. The synthesis features a three-step sequence to the epoxyquinol core that serves as a scaffold for the attachment of the polyene side chains. The eastern polyene side chain was constructed via a novel organozirconocene-mediated synthesis. Zirconocene methodology was also applied to the synthesis of the polyene side chains of asukamycin. The southern side chain of nisamycin was introduced via a Stille reaction that employed a vinyl bromo ketone, derived from an acid-sensitive bromo ketal. Pd-mediated coupling of the vinyl bromide with a stannyl TIPS ester gave TIPS-protected nisamycin that was readily converted to the natural product.

The synthesis of alisamycin, nisamycin, LL-C10037α and novel epoxyquinol and epoxyquinone analogues of manumycin A

Versatile synthetic routes are described for the preparation of a range of epoxyquinol and epoxyquinone analogues of the antitumour antibiotic manumycin A lacking the lower side chain, and these procedures have also been applied to prepare the bioactive natural product LL-C10037α. The extension of this methodology to provide a general synthetic route to the manumycin family of antibiotics is discussed and exemplified by the first total synthesis of alisamycin and ent-alisamycin. This route includes the novel, stereoselective organometallic addition of the Corey-Wollenberg reagent (E- 2-tributylstannylethenyllithium) to the manumycin nucleus and palladium catalysed Stille coupling technology for the introduction of the polyunsaturated 2-amino-3-hydroxycyclopentenone derived amide. Similar methodology has also been employed to complete the first total synthesis of the antibiotic nisamycin.