Synthesis and reactivity of a putative biogenetic precursor to tricholomenyns B, C, D and E

被引：12

作者：

Ma, Xinghua ^{[1
]}

Jury, Jasmine C. ^{[1
]}

Banwell, Martin G. ^{[1
]}

机构：

[1] Australian Natl Univ, Res Sch Chem, Inst Adv Studies, Canberra, ACT 0200, Australia

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 17期

基金：

澳大利亚研究理事会;

关键词：

Chemoenzymatic; Epoxy-quinol; Sonogashira reaction; Synthesis; Tricholomenyns; SELENIUM DIOXIDE; FRUITING BODIES; (-)-TRICHOLOMENYN; ACERBUM; OXIDATION; OLEFINS; ACID;

D O I：

10.1016/j.tetlet.2010.11.139

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A chemoenzymatic synthesis of the putative biogenetic precursor, 6, to the epoxy-quinol type natural products, tricholomenyns B, C, D and E (2-5, respectively), has been achieved. However, treatment of compound 6 under a variety of conditions failed to effect its conversion into any of the natural products 2-5. In contrast, the simple model system 22 reacts with acetic acid in the presence of stoichiometric quantities of Ti(OPr-i)(4) to give the diacetate 23. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：2192 / 2194

页数：3

共 40 条

[31] New pyrimido[5,4-e]pyrrolo[1,2-c]pyrimidines: Synthesis, 2D-QSAR, anti-inflammatory, analgesic and ulcerogenicity studies
Hanna, Mona M.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 : 12 - 22
[32] Synthesis and reactivity of pyrrolo[3,2-d][1,3]oxazine-2,4-dione. Access to new pyrrolo[3,2-e][1,4]diazepine-2,5-diones
Malcor, Jean-Daniel
Brouillette, Yann
Graffion, Julien
Spielmann, Kim
Masurier, Nicolas
Maillard, Ludovic T.
Martinez, Jean
Lisowski, Vincent
TETRAHEDRON, 2014, 70 (31) : 4631 - 4639
[33] Molecular Investigations of Novel Pyrano[2,3-c]Pyrazole Congeners as Potential HCoV-229E Inhibitors: synthesis, Molecular Modeling, 3D QSAR, and ADMET Screening
Abouelenein, Mohamed G.
El-boghdady, Aliaa H.
Ali, Hadeer M.
Said, Mohamed A.
POLYCYCLIC AROMATIC COMPOUNDS, 2025, 45 (02) : 251 - 268
[34] Synthesis and crystal structure of a new molecular complex of fullerene C70, 4BNDY·3C70·4C6H6 (BNDY is binaphtho[1,8-d,e]-1,3-dithiin-2-ylidene)
V. V. Gritsenko
O. A. D'yachenko
D. V. Konarev
R. N. Lyubovskaya
Russian Chemical Bulletin, 2000, 49 (1) : 102 - 105
[35] Synthesis and crystal structure of a new molecular complex of fullerene C70, 4BNDY•3C70•4C6H6 (BNDY is binaphtho[1,8-d,e]-1,3-dithiin-2-ylidene)
Gritsenko, VV
D'yachenko, OA
Konarev, DV
Lyubovskaya, RN
RUSSIAN CHEMICAL BULLETIN, 2000, 49 (01) : 102 - 105
[36] Synthesis and some conversions of partially hydrogenated 1-aminopyrano(thiopyrano)[4,3-d]-pyrazolo[3,4-b]pyridines and pyrazolo[3,4-c]isoquinolines
E. G. Paronikyan
S. N. Sirakanyan
A. S. Noravyan
Chemistry of Heterocyclic Compounds, 2003, 39 (3) : 374 - 378
[37] Synthesis, anticancer activity and effects on cell cycle profile and apoptosis of novel thieno[2,3-d]pyrimidine and thieno[3,2-e] triazolo[4,3-c]pyrimidine derivatives
Kandeel, Manal M.
Refaat, Hanan M.
Kassab, Asmaa E.
Shahin, Inas G.
Abdelghany, Tamer M.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 90 : 620 - 632
[38] Synthesis and biological evaluation of novel 6,11-dihydro-5H-benzo[e] pyrimido- [5,4-b][1,4]diazepine derivatives as potential c-Met inhibitors
Huang, Daowei
Huang, Lei
Zhang, Qingwei
Li, Jianqi
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 140 : 212 - 228
[39] Synthesis and Crystal Structure of (E)-Ethyl (9-bromo-5-oxo-4-phenyl-1,10b-dihydro-5H-pyrano[3,4-c]chromen-2-ylidene) Acetate
Wang Ying
Shi De-Qing
CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2013, 32 (04) : 521 - 524
[40] Monoclinic and orthorhombic forms of (RS)-(E)-4-[2-(4-chlorobenzylidene)hydrazinyl]-6,11-dimethyl-6,11-dihydro-5H-benzo[b]pyrimido[5,4-f]azepine: synthesis, concomitant polymorphism and supramolecular assembly mediated by C-H•••N, C-H•••π(arene) and C-Cl•••π(arene) interactions
Acosta Quintero, Lina M.
Palma, Alirio
Choquesillo-Lazarte, Duane
Cobo, Justo
Glidewell, Christopher
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2019, 75 : 686 - +

← 1 2 3 4 →