Enantio- and stereoselective route to the phoslactomycin family of antibiotics: formal synthesis of (+)-fostriecin and (+)-phoslactomycin B.
نویسندگان
چکیده
A general methodology applicable for the synthesis of the phoslactomycin family of antibiotics, potent and selective protein phosphatase inhibitors, has been developed starting from a beta-isocupreidine-catalyzed asymmetric Baylis-Hillman reaction of 3-(4-methoxybenzyloxy)propanal with hexafluoroisopropyl acrylate, and thereby formal syntheses of (+)-fostriecin and (+)-phoslactomycin B have been accomplished.
منابع مشابه
Lactomycins A–C, Dephosphorylated Phoslactomycin Derivatives That Inhibit Cathepsin B, from the Marine-Derived Streptomyces sp. ACT232
Three new polyketides, lactomycins A (1)-C (3), were isolated from the culture broth of a marine-derived Streptomyces sp. ACT232 as cathepsin B inhibitors. Their structures were determined by a combination of NMR and MS data analyses to be the dephosphorylated derivatives of a phoslactomycin class of metabolites. Lactomycins exhibited cathepsin B inhibitory activity (IC50 0.8 to 4.5 μg/mL). Eve...
متن کاملTotal synthesis of phoslactomycin A.
A convergent total synthesis of the PP2A-inhibitor phoslactomycin A was achieved using a CuTC-mediated coupling of an alkenyl iodide C1-C13 fragment with an C14-C21 alkenyl stannane in the presence of a protected phosphate. Key features for the assembly of the C1-C13 fragment were an asymmetric dihydroxylation, an Evans-Aldol reaction, and a well-balanced protective group strategy. An asymmetri...
متن کاملArticleLactomycins A-C
Three new polyketides, lactomycins A (1)–C (3), were isolated from the culture broth of a marine-derived Streptomyces sp. ACT232 as cathepsin B inhibitors. Their structures were determined by a combination of NMR and MS data analyses to be the dephosphorylated derivatives of a phoslactomycin class of metabolites. Lactomycins exhibited cathepsin B inhibitory activity (IC50 0.8 to 4.5 μg/mL). Eve...
متن کاملNovel microbial metabolites of the phoslactomycins family induce production of colony-stimulating factors by bone marrow stromal cells. II. Isolation, physico-chemical properties and structure determination.
Leustroducsins (LSNs) A, B and C, novel inducers of colony-stimulating factors (CSFs), were isolated from culture broth of Streptomyces platensis SANK 60191 mainly by ethyl acetate extraction and preparative reverse-phase HPLC. The molecular weights and molecular formulae of LSNs A, B and C are 641: C32H52O10NP, 669: C34H56O10NP and 669: C34H56O10NP, respectively. The structure elucidation reve...
متن کاملEnantio- and Diastereodivergent Synthetic Route to Multifarious Cyclitols from D-Xylose via Ring-Closing Metathesis.
Short stereoselective syntheses of various cyclitols, including the derivatives of conduritol B, conduritol F, myo-inositol and chiro-inositol, have been accomplished. The key steps in the syntheses are a ring-closing metathesis process and a diastereodivergent organometallic addition to a D-xylose-derived alde-hyde.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Chemical communications
دوره 39 شماره
صفحات -
تاریخ انتشار 2009