共查询到20条相似文献,搜索用时 0 毫秒
1.
A convergent and efficient formal synthesis of (±)-atisine has been accomplished. The synthetic strategy is to efficiently construct the bicyclo[2.2.2]octane ring moiety by an oxidative dearomatization/intramolecular Diels-Alder cycloaddition cascade. The first total synthesis of another atisine-type C(20)-diterpenoid alkaloid, (±)-isoazitine, has also been achieved employing the same strategy. 相似文献
2.
A concise total synthesis of (±)-minfiensine using all conventional methods and starting from commercial materials has been completed. The synthesis features a Fischer indole synthesis, a Heck alkylation of an intermediate ketone enolate, conversion of a ketone carbonyl into an epoxide, and transformation of the latter into an allylic alcohol. 相似文献
3.
Unsaturated eight-membered lactones undergo decarboxylative and non-decarboxylative transannular Ireland-Claisen rearrangement reactions, to give substituted vinylcyclobutanes. A formal synthesis of (±)-grandisol is described. 相似文献
4.
《Tetrahedron letters》1988,29(43):5525-5528
Dispiro[3.0.4.2] undecane 1 has been synthesized and rearranged to (±)modhephene 2 and triquinane 3 under kinetic control, and to (±)isocomene 4 and triquinane 5 under thermodynamic control. Molecular mechanics calculations (MM2) support the mechanism proposed. 相似文献
5.
We report the first total synthesis of (±)-trigonoliimine C, a member of a family of structurally complex alkaloids, in 10 steps from tryptamine and 6-methoxytryptamine. Our convergent synthetic strategy relies on a selective oxidative rearrangement of an unsymmetrical 2,2'-bis-tryptamine. 相似文献
6.
An acid-catalyzed intramolecular [4 + 2] cycloaddition of a non-natural bisabolene is reported. The key cyclocondensation was developed to access cyclic sesquiterpenes from linear phenolic precursors by generating a reactive o-quinone methide intermediate to initiate a cascade reaction. The new method was applied to the first total synthesis of (±)-heliol. 相似文献
7.
Using an intramolecular [4 + 2] cycloaddition/rearrangement cascade of 3-(1,4-dioxaspiro[4.4]non-7-en-7-yl)-N-furan-2-ylpropionamide (23) as the key step, the BCD core of the lycopodium alkaloid fawcettidine was constructed. Heating the initially formed Diels-Alder cycloadduct at 180 °C results in a nitrogen-assisted ring opening followed by a deprotonation/reprotonation of the ensuing zwitterion to give a rearranged hexahydroindolinone. Our attempts to induce a related intramolecular furan Diels-Alder reaction (IMDAF) from the corresponding ketone of 23 failed to give any cycloaddition product. Instead, the only product obtained corresponded to a cyclopentenone derivative derived by isomerization of the double bond into the thermodynamically more stable α,β-position. Efforts toward construction of the final skeleton of fawcettidine by ring A closure of the rearranged cycloadduct derived from furanyl amide 23 are discussed. 相似文献
8.
《Tetrahedron letters》1986,27(8):947-950
A new synthesis of tricyclic lactones via allene intramolecular cycloaddition and its application to synthesis of (±)-platyphyllide are described. 相似文献
9.
10.
11.
The pentacyclic alkaloid (±)-meloscine was prepared in 19 steps through a reaction sequence that features a putative azatrimethylenemethane intermediate, generated through cascade cyclization of an allenyl azide substrate, to deliver the core azabicyclo[3.3.0]octadiene substructure. Subsequent manipulation of the peripheral functionality then delivered (±)-meloscine. 相似文献
12.
《Tetrahedron letters》1988,29(11):1263-1264
The dispiro [3.0.4.2] undecanes 2 and 6 undergo cascade rearrangements yielding the [3.3.3]propellanes 3 and 7, respectively. The rearrangement of 6 proceeds regiospecifically and renders 9 a promising candidate for a direct conversion to (±)modhephene 10. 相似文献
13.
Vivek D. Bobade Pravin C. Mhaske Kamlesh S. Vadgaonkar Shivaji H. Shelke 《Monatshefte für Chemie / Chemical Monthly》2012,21(4):847-851
Abstract
Efficient utilization of a Mannich-type reaction and the ring-closing metathesis (RCM) approach that leads to a convenient synthesis of 3-(aminomethyl)-5-methylhexanoic acid (pregabalin) is described. 相似文献14.
《Tetrahedron letters》1986,27(4):445-448
A total synthesis of the mold metabolite ethisolide (1a) is described, wherein a glycolate ester enolate Claisen rearrangement and an acid-induced intramolecular bis-transesterification are key steps. 相似文献
15.
16.
The cascade reactions of alkyl α-diazoesters and ynones using Al(OTf)3 as the catalyst are described.A series of 4-substituted pyrazoles were obtained via [3+2] cycloaddition,1,5-ester shift,1,3-H shift,and N-H insertion process.Deuterium labelling experiments,kinetic studies and control experiments were carried out for the rationalization of the mechanism. 相似文献
17.
《Tetrahedron letters》1986,27(11):1293-1296
A total synthesis of the antiviral metabolite virantmycin is described. 相似文献
18.
Kobayashi S Kinoshita T Kawamoto T Wada M Kuroda H Masuyama A Ryu I 《The Journal of organic chemistry》2011,76(17):7096-7103
The potential of the oxy-Favorskii rearrangement to form branched cis-fused bicyclic ethers was explored. Both tertiary and quaternary centers were constructed in highly stereospecific manners. Methanol and primary amines were effective nucleophiles for the rearrangement. The total synthesis of (±)-communiol E was achieved based on this method. 相似文献
19.
A new synthetic route to (±)-pancratistatin was devised utilizing β-silyl styrene as a dienophile in the cycloaddition with 3,5-dibromo-2-pyrone. The TMS group incorporated in the cycloadduct permitted a facile elimination process for the eventual installation of the C(1)-OH function. Subsequent transformations including Curtius rearrangement and Bischler-Napieralski reactions completed the total synthesis of (±)-pancratistatin. 相似文献
20.
Yuzuki Yamamoto Naoki Mori Hidenori Watanabe Hirosato Takikawa 《Tetrahedron letters》2018,59(38):3503-3505
Pseudohygrophorones A12 and B12 are cyclohexenone derivatives isolated from Hygrophorus abieticola (Basidiomycete) as anti-phytopathogenic compounds. In this study, the first synthesis of (±)-pseudohygrophorones A12 is reported, utilizing Michael–aldol cascade reaction for constructing the 3,3-dimethyl-2,4-dioxabicyclo[3.1.1]nonan-9-one skeleton and the diastereoselective addition of alkyllithium to the one-side blocked ketone as the key steps. 相似文献