157097-82-0Relevant academic research and scientific papers
Synthesis and evaluation of a cyclopropane derivative of DHMEQ
Yasui, Eiko,Takayama, Kan,Nakago, Takahiro,Takeda, Nobuyuki,Imamura, Yasutada,Nagumo, Shinji
, p. 304 - 307 (2014/04/17)
Dehydroxymethylepoxyquinomycin (DHMEQ, 1) is well known to inhibit nuclear factor-kappa B (NF-κB), which is closely associated with immune, inflammatory, and apoptotic processes as an inducible transcription factor. The inhibitory effect seems to be the r
Total synthesis of (±)-nisamycin
Wipf, Peter,Coish, Philip D. G.
, p. 5053 - 5061 (2007/10/03)
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.
Synthesis of (-)-LL-C10037α and related manumycin-type epoxyquinols
Wipf,Kim,Jahn
, p. 1549 - 1561 (2007/10/02)
Starting with N-allyloxycarbonyl-protected 2,5-dimethoxyaniline, hypervalent iodine oxidation protocols and selective enone epoxidation provides the Streptomyces metabolite LL-C10037α in nine steps and 7-10% overall yield. In an asymmetric variant of this strategy, (R,R)-pentane-2,4-diol is used as a chiral acetalization agent. The resulting semiquinone spiroacetal, due to an ortho-acylamino substituent that restricts the 1,3-dioxane ring conformation, undergoes face-selective epoxidation and is further functionalized to give (-)-LL-C10037α in 94% ee. These pathways represent the first syntheses of the highly functionalized mC7N core of the manumycins and have been further extended toward the preparation of analogs for SAR studies of this class of antitumor antibiotics. Manumycins inhibit the farnesylation of Ras-protein by PFTase (protein farnesyltransferase).
Synthesis of the Antitumor Antibiotic LL-C10037α
Wipf, Peter,Kim, Yuntae
, p. 3518 - 3519 (2007/10/02)
(+/-)-LL-C10037α and its C(4)-epimer were prepared in nine steps from 2,5-dimethoxyaniline.The concise synthetic route represents the first synthesis of this highly functionalized antitumor antibiotic and is useful for the preparation of analogs of the putative pharmacophore of the Ras farnesyltransferase inhibitor manumycin
