Online citations, reference lists, and bibliographies.
← Back to Search

Tandem Oxidative Dearomatization/intramolecular Diels-Alder Reaction For Construction Of The Tricyclic Core Of Palhinine A.

C. Zhao, Huaiji Zheng, Peng Jing, B. Fang, X. Xie, Xuegong She
Published 2012 · Chemistry, Medicine

Cite This
Download PDF
Analyze on Scholarcy
Share
A concise construction of the 6/6/5 tricyclic core of Lycopodium alkaloid palhinine A (1) has been accomplished. The developed synthetic strategy featured a tandem oxidative dearomatization/intramolecular Diels-Alder reaction to construct C/D rings and an intramolecular 5-exo-trig radical cyclization to install the B ring of palhinine A (1). The developed approach paves the way for the total synthesis of palhinine A (1).
This paper references
10.1021/ol802251q
Zamamidines A and B, new manzamine alkaloids from the sponge Amphimedon species.
Y. Takahashi (2009)
10.1021/ol902389e
Total synthesis of (-)-lycoperine A.
Yoshitaka Nakamura (2010)
10.1021/JA00479A061
Olefin homologation with titanium methylene compounds
F. N. Tebbe (1978)
10.1039/B409720N
The Lycopodium alkaloids.
X. Ma (2004)
10.1002/HLCA.19780610840
Efficient Conversion of Esters to α‐Trimethylsilylketones. Preliminary communication
M. Demuth (1978)
10.1021/jo802295p
Efficient synthesis and subsequent transformations of phenylsulfanylbicyclo[2.2.2]octenones and phenylselenylbicyclo[2.2.2]octenones.
S. Gao (2009)
10.1021/ol902455y
Concise total syntheses of the Lycopodium alkaloids (+/-)-nankakurines A and B via luciduline.
Xiayun Cheng (2010)
10.1021/JO035008G
Synthesis of a Highly Hindered Hydrindanone via α-Carbonyl Radical Cyclization: Enantiospecific Formal Syntheses of (−)-Pinguisenol and (−)-α-Pinguisene
Chin-Kang Sha (2003)
10.1021/jo100916x
Development of an enantioselective route toward the Lycopodium alkaloids: total synthesis of lycopodine.
Hua Yang (2010)
10.1021/JO972073F
PRACTICAL SYNTHESIS OF ()-CHLOROVULONE II
Marco A. Ciufolini (1998)
10.1002/anie.201103550
Asymmetric total synthesis of a pentacyclic Lycopodium alkaloid: huperzine-Q.
A. Nakayama (2011)
10.1021/JO00274A034
Atom transfer cyclization reactions of .alpha.-iodo esters, ketones, and malonates: examples of selective 5-exo, 6-endo, 6-exo, and 7-endo ring closures
D. Curran (1989)
10.1021/JO9723570
alpha-Carbonyl Radical Cyclization Approach toward Angular Triquinanes: Total Synthesis of Enantiomerically Pure (-)-5-Oxosilphiperfol-6-ene.
Chin-Kang Sha (1998)
10.1021/ja804588r
An expedient asymmetric synthesis of platencin.
K. Nicolaou (2008)
10.1021/jo101619d
Total synthesis of (+)-nankakurines A and B and (±)-5-epi-nankakurine A.
R. A. Altman (2010)
10.1021/ol901963v
A synthesis of the carbon skeleton of maoecrystal V.
P. Krawczuk (2009)
10.1002/anie.201106753
Total syntheses of Lycopodium alkaloids (+)-fawcettimine, (+)-fawcettidine, and (-)-8-deoxyserratinine.
H. Li (2012)
10.1021/ol100823t
Methoxypyridines in the synthesis of Lycopodium alkaloids: total synthesis of (+/-)-lycoposerramine R.
Vishnumaya Bisai (2010)
10.3987/REV-08-SR(F)6
The Lycopodium alkaloids.
J. Kobayashi (2005)
10.1021/JA00433A062
Multiple metal-carbon bonds. 5. The reaction of niobium and tantalum neopentylidene complexes with the carbonyl function
R. R. Schrock (1976)
10.1021/JA00033A087
Synthetic studies on quassinoids: total synthesis of simalikalactone D and assignment of the absolute configuration of the .alpha.-methylbutyrate ester side chain.
E. Moher (1992)
10.1021/ja101893b
Total synthesis of (+)-complanadine A using an iridium-catalyzed pyridine C-H functionalization.
D. Fischer (2010)
10.1021/JA00349A082
Free-radical cyclization of bromo acetals. Use in the construction of bicyclic acetals and lactones
G. Stork (1983)
10.1021/ol901519k
Rapid assembly of vinigrol's unique carbocyclic skeleton.
Jason G. M. Morton (2009)
10.1007/128_2011_126
Lycopodium alkaloids: isolation and asymmetric synthesis.
M. Kitajima (2012)
10.1021/ja103666n
Total synthesis of (+)-sieboldine A.
Stephen M. Canham (2010)
10.1002/anie.200800522
Total synthesis of (+)-fawcettidine.
Jennifer A. Kozak (2008)
10.1021/ja109516f
Concise total synthesis of (+)-lyconadin A.
T. Nishimura (2011)
10.1021/ja107533m
Synthesis of the lycopodium alkaloid (+)-lycoflexine.
J. Ramharter (2010)
10.1021/ja804624u
Enantioselective total syntheses of nankakurines A and B: confirmation of structure and establishment of absolute configuration.
B. Nilsson (2008)
10.1002/anie.200907248
Total synthesis of (+)-clavolonine, (-)-deacetylfawcettiine, and (+)-acetylfawcettiine.
Kai M Laemmerhold (2010)
10.1021/JO0007480
Total syntheses of epothilones B and D.
J. Mulzer (2000)
10.1021/ol8026768
Study of very reactive tautomeric phenol dienones as dienes in Diels-Alder reactions.
Y. Dory (2009)
10.1021/jo1023188
Application of the Helquist annulation in Lycopodium alkaloid synthesis: unified total syntheses of (-)-8-deoxyserratinine, (+)-fawcettimine, and (+)-lycoflexine.
Y. Yang (2011)
10.1021/jo100499h
Total syntheses of (+)-fawcettimine and (+)-lycoposerramine-B.
Yasunari Otsuka (2010)
10.1021/ja104575h
Total synthesis of (+)-fastigiatine.
Brian B Liau (2010)
10.1002/ANIE.200702695
Total synthesis of (+)-fawcettimine.
X. Linghu (2007)
10.1021/ja108907x
Total synthesis of (±) maoecrystal V.
Jianxian Gong (2010)
10.1021/ja101956x
Synthesis of (+)-complanadine A, an inducer of neurotrophic factor excretion.
C. Yuan (2010)
10.1021/ja900536d
Total synthesis of the lycopodium alkaloid (+)-serratezomine A.
Aroop Chandra (2009)
10.1021/ol101602n
Palhinine A, a novel alkaloid from Palhinhaea cernua.
Fu-wei Zhao (2010)
10.1021/JA983631Q
Total Synthesis of Phomazarin
D. Boger (1999)
10.1021/ol902437t
First asymmetric total syntheses of fawcettimine-type Lycopodium alkaloids, lycoposerramine-C and phlegmariurine-A.
A. Nakayama (2009)
10.1021/jo1019688
Asymmetric synthesis of all the known phlegmarine alkaloids.
Bradley H Wolfe (2010)
10.1021/ol1009762
Enantiospecific formal total synthesis of (+)-fawcettimine.
M. Jung (2010)
10.1021/ja806865u
Explorations into neolignan biosynthesis: concise total syntheses of helicterin B, helisorin, and helisterculin A from a common intermediate.
S. Snyder (2009)
10.1021/ja804939r
The lyconadins: enantioselective total syntheses of (+)-lyconadin A and (-)-lyconadin B.
Douglas C. Beshore (2008)
Radical Cyclization Reaction Scheme 4
F. Zhao (2010)
10.1021/CR0306900
Cyclohexadienone ketals and quinols: four building blocks potentially useful for enantioselective synthesis.
D. Magdziak (2004)
10.1016/0040-4020(94)00961-S
Cyclobutanone-based tandem free radical rearrangements: Formation of bicyclic and tricyclic ketones
P. Dowd (1995)
10.1002/anie.201008147
Total synthesis of (±)-alopecuridine and its biomimetic transformation into (±)-sieboldine A.
X. Zhang (2011)



This paper is referenced by
10.1039/d0qo00554a
An approach towards the construction of the tetracyclic skeleton of palhinine alkaloids
Congcong Han (2020)
10.1002/asia.201200964
Concise formal syntheses of the Amaryllidaceae alkaloids (±)-tazettine and (±)-6a-epipretazettine: construction of the core skeleton via tandem intramolecular oxidative Friedel-Crafts/aza-Michael reaction.
Donghui Ma (2013)
10.1021/ol401411m
Isopalhinine A, a unique pentacyclic Lycopodium alkaloid from Palhinhaea cernua.
Liao-Bin Dong (2013)
10.1002/EJOC.201201754
Can Diels–Alder Reactions Lead to trans-Fused Products? A Computational Study of the Competitive [4+2] and [2+4] Cycloaddition of Dienes to α-Aryl-Substituted Cyclohexenones
Snezhana M. Bakalova (2013)
10.3390/molecules25184211
Strategies and Efforts towards the Total Synthesis of Palhinine Alkaloids
Yu-Yan Liang (2020)
10.1021/ol301534r
Toward the total synthesis of palhinine A: expedient assembly of multifunctionalized isotwistane ring system with contiguous quaternary stereocenters.
Guo-Biao Zhang (2012)
10.1039/C2GC36379H
Catalyst-free synthesis of diversely substituted 6H-benzo[c]chromenes and 6H-benzo[c]chromen-6-ones in aqueous media under MWI
Y. He (2012)
10.1021/jo501407z
Diels-Alder reactions of chiral isoimidium salts: a computational study.
S. Bakalova (2014)
10.1016/J.TET.2014.02.048
Intramolecular Diels–Alder reaction as a key step in tandem or sequential processes: a versatile tool for the synthesis of fused and bridged bicyclic or polycyclic compounds
P. Parvatkar (2014)
10.1002/anie.201410257
Intermolecular enantioselective dearomatization reaction of β-naphthol using meso-aziridine: a bifunctional in situ generated magnesium catalyst.
Dongxu Yang (2015)
10.1039/C6QO00222F
Efficient construction of the A/C/D tricyclic skeleton of palhinine A
Shuangshuang Duan (2016)
10.1002/anie.201809130
Biomimetic Syntheses of (±)-Isopalhinine A, (±)-Palhinine A, and (±)-Palhinine D.
C. Chen (2018)
10.1021/jo5011125
Substituted 3-E-styryl-2H-chromenes and 3-E-styryl-2H-thiochromenes: synthesis, photophysical studies, anticancer activity, and exploration to tricyclic benzopyran skeleton.
R. Roy (2014)
10.1039/c5cc06923h
Domino intramolecular Diels-Alder reactions to construct a 6/6/5/5 fused tetracyclic framework.
Gaoyuan Zhao (2015)
10.1021/ol501960j
Bioinspired total synthesis of gymnothelignan N.
H. Li (2014)
10.1007/s11426-016-0059-7
A strategic study towards constructing the nine-membered azonane ring system of palhinine A via an azidoketol fragmentation reaction
Fang-Xin Wang (2016)
10.1002/9781118754887.CH15
15. Dearomatization Reactions
F. Pigge (2015)
10.1039/C8QO01235K
A concise approach to the tricyclic framework of longipinane- and ent-longipinane-type sesquiterpenoids
M. He (2019)
10.1021/jacs.6b13401
Total Synthesis of Lycopodium Alkaloids Palhinine A and Palhinine D.
Fang-Xin Wang (2017)
10.1021/ol402689b
Synthesis of indole substituted twistenediones from a 2-quinonyl boronic acid.
Jaime Rojas-Martín (2013)
10.1002/EJOC.201201670
Reaction of Nitrile Oxides with Masked o‐Benzoquinones; Synthesis of Highly Functionalized Isoxazolines
Santhosh Kumar Chittimalla (2013)
10.1002/anie.201910129
Total Synthesis of (-)-Himeradine A.
S. Rychnovsky (2019)
10.1021/ol4033495
Studies toward the synthesis of palhinine lycopodium alkaloids: a Morita-Baylis-Hillman/intramolecular Diels-Alder approach.
N. Sizemore (2014)
Semantic Scholar Logo Some data provided by SemanticScholar