199658-05-4Relevant academic research and scientific papers
Attempts towards the synthesis of mupirocin-H
Bommagani, Shobanbabu,Thodupunuri, Prashanth,Sharma, Gangavaram V.M.
, p. 20 - 33 (2017/06/19)
The stereoselective synthesis of segments C1-C6 (3), C7-C12 (4) of mupirocin-H has been achieved. The synthetic procedure for the C1-C6 segment includes the zinc mediated allyl Grignard reaction with Rglyceraldehyde, Swern oxidation/Witting olefination reactions and followed by Sharpless asymmetric epoxidation. The C7-C12 segment was synthesized using again Sharpless asymmetric epoxidation on mono PMB protected 2-butene-1,4-diol, followed by regioselective opening of this epoxide with trimethyl aluminium. Both segments C1-C6 (3) and C7-C12 (4) possesses the five new stereogenic centers along with trans-olefin, but in various attempts condensation of 3 and 4 segments to give C-C bond forming parent segment (2) not affirmed, hence this work constitutes the synthesis of fragments C1-C6 (3) and C7-C12 (4) of mupirocin-H. {figure presented}
Total Synthesis of Leupyrrins A1 and B1, Highly Potent Antifungal Agents from the Myxobacterium Sorangium cellulosum
Thiede, Sebastian,Wosniok, Paul R.,Herkommer, Daniel,Debnar, Thomas,Tian, Maoqun,Wang, Tongtong,Schrempp, Michael,Menche, Dirk
supporting information, p. 3300 - 3320 (2017/03/16)
Full details on the design, elaboration, and application of efficient strategies for the high-yielding total syntheses of leupyrrins A1 and B1, unique antifungal agents from the myxobacterium Sorangium cellulosum, are reported. A sequential zirconocene-mediated diyne-cyclization, and regioselective opening of the zirconacyclopentadiene intermediate enabled a concise entry into the unique dihydrofuran fragment, whereas another domino reaction was developed for the butyrolactone involving a one-pot lactol opening, stereoselective aldehyde addition and in situ lactonization. Furthermore, an innovative sp2-sp3-cross-coupling for pyrrole functionalization and an optimized HATU-mediated amide coupling protocol of two elaborate fragments were established. In addition, an unusual protective group strategy, involving a Teoc-acetonide protected amine in combination with tert-butyl and acetate esters, was successfully elaborated. These tactics and strategies are generally useful and may be also applied in the synthesis of other functionalized compounds. It is expected that the material which was obtained by these total syntheses will enable the further exploration of the biological profile of these potent antifungal agents.
Stereoselective Synthesis of Isochromanones by an Asymmetric Ortho-Lithiation Strategy: Synthetic Access to the Isochromanone Core of the Ajudazols
Essig, Sebastian,Menche, Dirk
, p. 1943 - 1966 (2016/03/15)
Full details on the design, development, and application of a highly stereoselective strategy for the synthesis of isochromanones are reported. The method is based on an asymmetric ortho lithiation with aldehyde electrophiles and utilizes the chiral memor
Gold-catalyzed Hosomi-Sakurai type reaction for the total synthesis of herboxidiene
Thirupathi, Barla,Mohapatra, Debendra K.
, p. 6212 - 6224 (2016/07/11)
Total synthesis of herboxidiene/GEX1A/TAN-1609 has been accomplished in the 22 longest linear sequences starting from 2-butyne-1,4-diol following our recently developed gold-catalyzed Hosomi-Sakurai type of reaction on lactols with allyltrimethyl silane a
Catalytic diastereoselective reduction of α,β-epoxy and α,β-aziridinyl ynones
Druais, Valerie,Meyer, Christophe,Cossy, Janine
, p. 516 - 519 (2012/03/26)
The Noyori transfer hydrogenation of α,β-epoxy and α,β-aziridinyl ynones leads to the corresponding α,β-epoxy or α,β-aziridinyl propargylic alcohols with high reagent-controlled diastereoselectivity.
Asymmetric synthesis of triacetyl-d-erythro-sphingosine and D-1-deoxyallonojirimycin via Miyashita C2 selective endo-mode azide opening of 2,3-epoxy alcohol
Sridhar,Srinivas,Rao, K. Rama
experimental part, p. 10701 - 10708 (2010/01/16)
An efficient protocol for the asymmetric synthesis of triacetyl-d-erythro-sphingosine and D-1-deoxyallonojirimycin has been developed starting from commercially available propargyl alcohol. The key steps involved Sharpless asymmetric epoxidation and Miyashita C2 selective endo-mode azide opening of the 2,3-epoxy alcohol.
Total syntheses of the highly potent anti-cancer polyacetylenes, (S)-18-hydroxyminquartynoic acid, (S)-minquartynoic acid and (E)-15,16-dihydrominquartynoic acid
Sabitha, Gowravaram,Reddy, Ch. Srinivas,Yadav
, p. 4513 - 4516 (2007/10/03)
The total syntheses of three polyacetylenic natural products, (S)-18-hydroxyminquartynoic acid (1), (S)-minquartynoic acid (2) and (E)-15,16-dihydrominquartynoic acid (3), has been achieved. The Cadiot-Chodkiewicz cross-coupling reaction was used as the k
Enantioselective total synthesis of bistramide A
Crimmins, Michael T.,DeBaillie, Amy C.
, p. 4936 - 4937 (2007/10/03)
The enantioselective synthesis of bistramide A has been achieved with a longest linear sequence of 18 steps. The synthetic strategy involves the use of a distereoselective glycolate alkylation, an aldol addition of a chlorotitanium enolate of N-acylthiazolidinthione, and a Sharpless asymmetric epoxidation to synthesize the three key fragments. Copyright
Dicarboxamide derivatives
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Page/Page column 69-70, (2008/06/13)
The invention is concerned with novel dicarboxamide derivatives of formula (I) wherein A, B, Rc, D and E are as defined in the description and in the claims, as well as physiologically acceptable salts thereof. These compounds inhibit the coagulation factor Xa and can be used as medicaments.
Synthesis of the EF-ring segment of ciguatoxin CTX1B based on novel regioselective reduction of unsaturated cyanohydrins and ring-closing olefin metathesis
Takemura, Atsushi,Fujiwara, Kenshu,Shimawaki, Ken,Murai, Akio,Kawai, Hidetoshi,Suzuki, Takanori
, p. 7392 - 7419 (2007/10/03)
Aiming at a convergent total synthesis of ciguatoxin CTX1B, its EF-ring segment has been synthesized. During the synthesis, a novel method for the construction of branched ethers, based on regioselective reduction of γ-alkoxy β,γ-unsaturated α-silyloxy ni
