90367-65-0Relevant academic research and scientific papers
Synthesis of brassinolide and its biosynthetic precursors using methyl 3-hydroxy-2-methylpropionate
Khripach,Zhabinskii,Parkhimovich,Gulyakevich
experimental part, p. 240 - 249 (2010/04/26)
Formal synthesis of plant hormones that belong to the group of 24α-methylbrassinosteroids, including brassinolide and its biosynthetic precursors with one hydroxyl group in their side chain, was performed. Stereochemistry of a methyl group at the C24 atom
Total synthesis of khafrefungin using highly stereoselective vinylogous Mukaiyama aldol reaction
Shirokawa, Shin-Ichi,Shinoyama, Mariko,Ooi, Isao,Hosokawa, Seijiro,Nakazaki, Atsuo,Kobayashi, Susumu
, p. 849 - 852 (2007/10/03)
(Chemical Equation Presented) A convergent total synthesis of khafrefungin was accomplished on the basis of (1) the highly stereoselective TiCl 4-mediated vinylogous Mukaiyama aldol reaction using vinylketene silyl N,O-acetal and (2) syn-select
Synthesis of bistramide A
Statsuk, Alexander V.,Liu, Dong,Kozmin, Sergey A.
, p. 9546 - 9547 (2007/10/03)
We have developed an efficient and highly stereocontrolled synthesis of bistramide A, a selective activator of protein kinase C isotype δ. Our synthetic strategy featured a novel bidirectional approach for spiroketal construction based on the ring-opening
Chemistry and biology of khafrefungin. Large-scale synthesis, design, and structure-activity relationship of khafrefungin, an antifungal agent
Nakamura, Masayuki,Mori, Yuichiro,Okuyama, Kennichi,Tanikawa, Kunihiro,Yasuda, Satoshi,Kanada, Kentaro,Kobayashi, Shu
, p. 3362 - 3376 (2007/10/03)
Large-scale synthesis, design, and structure-activity relationships of khafrefungin are reported. Khafrefungin is an antifungal agent that inhibits inositol phosphorylceramide (IPC) synthase, a enzyme involved in fungal sphingolipid biosynthesis. Unlike o
Efficient total synthesis of khafrefungin: Convergent approach using Suzuki coupling under thallium-free conditions toward multigram-scale synthesis
Mori, Yuichiro,Nakamura, Masayuki,Wakabayashi, Takeshi,Mori, Kouhei,Kobayashi, Shu
, p. 601 - 603 (2007/10/03)
An efficient and practical synthetic route to khafrefungin, an antifungal agent, has been developed based on successive coupling of three components, 3, 4, and then 2. A key step of the synthesis is the Suzuki coupling of 2 and 10, in which the use of tox
Total Synthesis of (+)-Latrunculin A, an Ichthyotoxic Metabolite of the Sponge Latrunculia magnifica, and Its C-15 Epimer
White, James D.,Kawasaki, Motoji
, p. 5292 - 5300 (2007/10/02)
Latrunculin A (1), an ichthyotoxic metabolite of the sponge Latrunculia magnifica with potent inhibitory action on microfilament-mediated processes involved in cell division, was synthesized via a convergent approach.Construction of a major segment of the latrunculin backbone was accomplished by means of a three-component coupling of aldehyde 24, β-keto ester 27, and phosphonium salt 26, which established the conjugated E,Z-diene moiety of 31.The thiazolidinone subunit of 1 was elaborated in the form of 39 from L-cysteine and was linked to 35 without nitrogen protection.Final lactonization of 47 was carried out using the Mitsunobu protocol.A parallel sequence employing the epimeric seco acid 48 produced 15-epilatrunculin A.
Diastereofacial Selection in Nitrile Oxide Cycloaddition Reactions. The Anti-Directing Effect of an Allylic Oxygen and Some New Results on the Ring Metalation of Isoxazolines. A Synthesis of (+/-)-Blastmycinone
Kozikowski,, Alan P.,Ghosh, Arun K.
, p. 2762 - 2772 (2007/10/02)
The extent of diastereoselectivity associated with the reactions of nitrile oxides with alkenes bearing an allylic oxygen substituent has been studied.Reasonable levels of such diastereoselectivity have been found when the tert-butyldimethylsilyl ether derivative of 3-buten-2-ol (5) or (+)-(S)-isopropylidene-3-butene-1,2-diol (1) are employed as dipolarophiles.The stereochemical course of these cycloaddition reactions has been proven rigorously through the transformation of the adducts to known γ-lactones.The stereochemistry associated with the metalation/alkylation of 5-alkoxymethyl-substituted isoxazolines has also been probed in order to further expand the use of these heterocycles as aldol equivalents in natural products total synthesis.A synthesis of (+/-)-blastmycinone (34) is reported which combines the two foregoing aspects of stereocontrol.The levels of regio- and stereoselectivity found in the cycloaddition reactions of the cis- and trans-disubstituted alkenes 35 and 39 prepared from isopropylidene-D-glyceraldehyde are also discussed.A single example of the reaction of a chiral alkene with a chiral nitrile is presented.
