151409-24-4Relevant academic research and scientific papers
Synthesis of Non-natural, Frame-Shifted Isoprenoid Diphosphate Analogues
Temple, Kayla J.,Wright, Elia N.,Fierke, Carol A.,Gibbs, Richard A.
, p. 6038 - 6041 (2016)
A set of synthetic approaches was developed and applied to the synthesis of eight frame-shifted isoprenoid diphosphate analogues. These analogues were designed to increase or decrease the methylene units between the double bonds and/or the pyrophosphate m
Efficient Construction of (±)- epi -Costunolide through a Chromium(II)-Mediated Nozaki-Hiyama-Kishi Reaction
Dai, Weichen,Zheng, Jie,Yan, Xinyu,Tang, Wei,Hu, Lihong,Zhang, Yinan
supporting information, p. 1469 - 1472 (2021/07/25)
(±)- epi -Costunolide has been synthesized through a seven-step procedure starting from (E, E)-farnesol. The key step includes an intramolecular allylation of an aldehyde through a chromium(II)-mediated Nozaki-Hiyama-Kishi reaction, in which more than one equivalent of CrCl 2has been recognized as the most effective reagent to promote the conversion. An anti-inflammatory screen showed that epi -costunolide is a moderate inhibitor of B lymphocyte proliferation.
ISOPRENE OLIGOMER, POLYISOPRENE, PROCESSES FOR PRODUCING THESE MATERIALS, RUBBER COMPOSITION, AND PNEUMATIC TIRE
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Paragraph 199-200, (2014/06/25)
The invention relates to an isoprene oligomer that contains a trans structural moiety and a cis structural moiety, which can be represented by the following formula (1), wherein at least 1 atom or group in the trans structural moiety is replaced by another atom or group. The invention also relates to a polyisoprene, which is biosynthesized using the isoprene oligomer and isopentenyl diphosphate. Further, this invention provides a rubber composition comprising the isoprene oligomer and/or the polyisoprene, and a pneumatic tire, including tire components (e.g., treads and sidewalls) formed from the rubber composition. wherein n represents an integer from 1 to 10; m represents an integer from 1 to 30; and Y represents a hydroxy group, a formyl group, a carboxy group, an ester group, a carbonyl group, or a group represented by the following formula (2):
Total syntheses of parthenolide and its analogues with macrocyclic stereocontrol
Long, Jing,Zhang, Shan-Feng,Wang, Pan-Pan,Zhang, Xue-Mei,Yang, Zhong-Jin,Zhang, Quan,Chen, Yue
, p. 7098 - 7112 (2014/11/08)
The first total synthesis of parthenolide (1) is described. The key feature of this synthesis is the formation of a 10-membered carbocylic ring by a macrocyclic stereocontrolled Barbier reaction, followed by a photoinduced Z/E isomerization. The biological evaluation of a small library of parthenolide analogues (19, 33, and 34) disclosed a preliminary structure-activity relationship (SAR). The results revealed that the C1, C10 double bond configuration of parthenolide has little or no effect on the activity, and the C6 and C7 configurations of the lactone ring have a moderate impact on the activities against some cancer cell lines.
Biomimetic cyclization of epoxide precursors of indole mono-, sesquiand diterpene alkaloids by lewis acids
Isaka, Tetsuya,Hasegawa, Morifumi,Toshima, Hiroaki
experimental part, p. 2213 - 2222 (2012/02/14)
Cyclization of the synthesized epoxide precursors of indole mono-, sesqui- and diterpene alkaloids was performed to elucidate the mechanism for biomimetic cationic cyclization to polycyclic structures. 3-(6,7- Epoxygeranyl)indole (11), 3-(10,11-epoxyfarne
Acid-catalyzed cyclization of terpenes under homogeneous and heterogeneous conditions as probed through stereoisotopic studies: A concerted process with competing preorganized chair and boat transition states
Raptis, Christos,Lykakis, Ioannis N.,Tsangarakis, Constantinos,Stratakis, Manolis
supporting information; experimental part, p. 11918 - 11927 (2010/04/28)
Based on stereoisotopic studies and β-secondary isotope effects, we propose that the acid-catalyzed cyclization of geranyl acetate proceeds through a concerted mechanism. Under heterogeneous conditions (zeolite Y confinement), a preorganized chairlike transition state predominates, whereas under homogeneous conditions the boat-and chairlike transition states are almost isoenergetic. For the case of farnesyl acetate, we propose that under homogeneous conditions a concerted dicyclization occurs with a preorganized boat-chair transition state competing with the chair-chair transition state. Under zeolite confinement conditions, the chair-chairlike dicyclization transition state is highly favorable. The preference of chairlike transition states within the cavities of zeolite Y is attributed to a transition state shape selectivity effect.
Synthesis of (2E,6E)-[10-3H]farnesol and (2E,6E)-[10-3H]farnesal for insect dehydrogenase studies
Sen,Garvin
, p. 1063 - 1069 (2007/10/02)
[10-3H]Farnesol ((2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-ol) and [10-3H]farnesal ((2E,6E)-3,7,11-trimethyl-2,6,10- -dodecatrian-1-al) were synthesized by sequential reduction and oxidation of the corresponding tert-butyldiphenylsilyl protected 11,12,13-trisnoraldehyde, followed by Wittig homologation using isopropyltriphenylphosphorane. Direct reduction of the C-12 allylic bromide or allylic chloride proved to be an nonviable method, resulting in either multiple decomposition products or significant double bond transposition. Oxidation of the [10-3H]labelled trisnoralcohol with pyridinium chlorochromate resulted in essentially complete retention of the radiolabel as was established for the corresponding deuterated material. [3H]labelled farnesol and farnesal were obtained in 78% and 74% yields, respectively, from the trisnoraldehyde. These materials were used as radiotracers for examining the enzymatic activity of insect farnesol and farnesal dehydrogenase, key enzymes in the biosynthesis of juvenile hormone.
A BIOMIMETIC CHEMICAL SYNTHESIS OF HUMULENE FROM FARNESOL
Corey, E. J.,Daigneault, Sylvain,Dixon, Brian R.
, p. 3675 - 3678 (2007/10/02)
The first synthesis of humulene (1) by a biomimetic cation-olefin cyclization route is reported.
