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Tetrahedron Letters Vol. 53, No. 10, 2012
Contents
COMMUNICATIONS
Manipulating reduction potentials in an artificial safranin cofactor pp 1201–1203
Gheevarghese Raju, Joseph Capo, Bruce R. Lichtenstein, Jose F. Cerda, Ronald L. Koder*
H2N
O
N
N
A modular approach to the synthesis of 1,4,5-substituted-2-aminoimidazoles pp 1204–1206
Zhaoming Su, Lingling Peng, Christian Melander*
Direct oxidative conversion of 3-aryl propionaldehydes to 3-aryl acroleins promoted by SOMO catalysis pp 1207–1209
Jin Zhu, Shunting Yu*, Wenchao Lu, Jing Deng, Jian Li, Wei Wang*
Ar O
Tetrahedron Letters
journal homepage: www.elsevier.com/locate/tetlet
NH2
O N
Ph
(20 mol%)
N
H
CAN (1.5 equiv.)
Ar O
25 o C, DME 60-90% yields
13 examples
1193

1194 Contents / Tetrahedron Letters 53 (2012) 1193–1199
Palladium-catalyzed bisfunctionalization of active alkenes by b-acetonitrile-a-allyl addition: application to the
synthesis of unsymmetric 1,4-di(organo)fullerene derivatives
Shirong Lu, Tienan Jin*, Ming Bao, Abdullah M. Asiri, Yoshinori Yamamoto*
R
CN
CN
+
O
O
CN
5 mol% Pd2dba3•CHCl3 20 mol% BINAP CN
THF, rt
CN
R CN
pp 1210–1213
Site-specific incorporation of 5-methylaminomethyl-2-thiouridine and 2-thiouridine(s) into RNA sequences pp 1214–1217
Grazyna Leszczynska, Jakub Pie˛ta, Piotr Leonczak, Agnieszka Tomaszewska, Andrzej Malkiewicz*
Novel bis[(E)-1-(halomethyl)-2-chlorovinyl] chalcogenides as starting materials for the efficient synthesis of
bis(chloromethylidene)-1,4-dichalcogenanes
Alexander V. Martynov, Lyudmila I. Larina, Svetlana V. Amosova*
1
X
ZCl 2
CHCl 3
X X
Cl Cl
Z
2
X = Br, Na2A A
EtOH, - NaBr
Cl
Z
3
Cl
1: X = Br, Cl;
2: Z = S, X = Br, Cl; Z = Se, X = Br;
3: Z = A = S; Z = A = Se;
Z = Se, A = S; Z = S, A = Se
Unsymmetrical N and/or O-bridged calixarene derivatives: synthesis, structure and encapsulation of solvent
molecules in the solid state
Jingjing Yuan, Yanping Zhu, Mi Lian, Qinghe Gao, Meicai Liu, Fengcheng Jia, Anxin Wu*
pp 1218–1221
pp 1222–1226

Leucomidines A–C, novel alkaloids from Leuconotis griffithii pp 1227–1230
Midori Motegi, Alfarius Eko Nugroho, Yusuke Hirasawa, Takashi Arai, A. Hamid A. Hadi, Hiroshi Morita*
Two novel indole alkaloids and new quinazoline alkaloids, namely leucomidines A–C (1–3), were isolated from the barks of Leuconotis griffithii. The structures including the
absolute configuration were elucidated on the basis of spectroscopic data, chemical means, and CD calculations. The quinazoline alkaloid, 3, is proposed to be derived from the
same biogenetic precursor as the indole alkaloids 1 and 2.
The first examples of seco-prezizaane-type norsesquiterpenoids with neurotrophic activity from Illicium jiadifengpi pp 1231–1235
Miwa Kubo*, Kana Kobayashi, Jian-Mei Huang, Kenichi Harada, Yoshiyasu Fukuyama*
O
O
HO
HO
OH
O
O
O
H
1 2
OH
OH
O
O
Enantioselective total synthesis of heliespirone B pp 1236–1239
Akari Miyawaki, Yuki Manabe, Masahiro Yoshida, Kozo Shishido*
Synthesis, structures, and ligating ability of 4-tert-butylcalix[n]arene (iso)nicotinoylate pp 1240–1244
Eun Ji Kim, Jungmin Ahn, Haeri Lee, Tae Hwan Noh*, Ok-Sang Jung*
OH OH
m 2
N
Contents / Tetrahedron Letters 53 (2012) 1193–1199 1195
O
Cl
O O OH
N
m
2
CoCl2
= 1a

1196 Contents / Tetrahedron Letters 53 (2012) 1193–1199
Asymmetric synthesis of highly functionalized c-lactams through an organocatalytic aza-Michael–Michael reaction
cascade using fumaric acid amide esters as multi-reactive substrates
Takuya Yokosaka, Akinari Hamajima, Tetsuhiro Nemoto, Yasumasa Hamada*
pp 1245–1248
Synthesis of ruthenium tris(2,2 0 -bipyridine)-type complexes tethered to peptides at 5,5 0 -positions pp 1249–1252
Yoshimi Shiina, Shigero Oishi, Hitoshi Ishida*
One-pot, three-component synthesis of 1-amidomethyl-imidazo[1,2-a]pyridines catalyzed by ytterbium triflate pp 1253–1257
Kasiviswanadharaju Pericherla, Bharti Khungar, Anil Kumar*
R
N
Ar CHO
N
+
H 3 C
R 2
O
R 1
NH 2
Yb(OTf) 3
1,4-Dioxane
120 ºC, 12h
R
N
Ar
N
R 2
NH
CH
O 3
First stereoselective total synthesis of pectinolide H pp 1258–1260
D. Ramesh, V. Shekhar, D. Chantibabu, S. Rajaram, U. Ramulu, Y. Venkateswarlu*
O
OAc
O O O
O
R 1
OAc OH
Pectinolide H
O
O

Microwave-assisted multicomponent reaction of aryl amidines: regiospecific synthesis of new polysubstituted
thiopyrano-, and pyrano[4,3-d]pyrimidines
Bo Jiang*, Li-Yuan Xue, Xing-Han Wang, Man-Su Tu, Yin-Ping Liu, Shu-Jiang Tu*
Ar
Ο + 2
O
X
Ar'
+ HN NH2 Ar'
N N
Base
MW
Ar Ar
X = O, S X
pp 1261–1264
Solvent-free copper-catalyzed N-arylation of amino alcohols and diamines with aryl halides pp 1265–1270
Huiqing Yin, Ming Jin, Wei Chen, Chen Chen, Likang Zheng, Ping Wei, Shiqing Han*
R 1
+
X
R2 HN
R3 CuCl 10 mol %
KOH 2 equiv
Concise total syntheses of Marinoquinolines A–C pp 1271–1274
Lijun Ni, Ziyuan Li, Fan Wu, Jinyi Xu, Xiaoming Wu, Lingyi Kong, Hequan Yao*
Me
NHAc
+
O O
S
TosMIC
COOEt
N
Leusen's Pyrrole
synthesis
Base
Contents / Tetrahedron Letters 53 (2012) 1193–1199 1197
EtOOC
O
NH
R
NH
R 1
Mogen-Walls
reaction
1) POCl 3
N R 2
R 3
2) Decarboxylation
N
NH
Marinoquinoline A R=CH 3
Marinoquinoline B R=CH 2CH(CH 3) 2
Marinoquinoline C R=Bn
Amine-directed intramolecular hydroacylation of alkenes and alkynes pp 1275–1277
Holly D. Bendorf*, Kyle E. Ruhl, Andrew J. Shurer, Jennie B. Shaffer, Tess O. Duffin, Theresa L. LaBarte, Michelle L. Maddock,
Oscar W. Wheeler
X
CHO
Rh(I) catalyst
N n
R R' n=1,2 X N
X = CH, N
R
O
R'
n
R

1198 Contents / Tetrahedron Letters 53 (2012) 1193–1199
Rapid access to pyrido[1,2,5]triazepin-4-ones through intramolecular nucleophilic aromatic substitution pp 1278–1281
Shujuan Jin*, Olivier St-Jean, Sandra I. Baltatu, Vijayaratnam Santhakumar, Mirosław J. Tomaszewski
Novel route to spiropiperidines using N-methyl-4-piperidone, malononitrile and electrophiles pp 1282–1286
Neelakandan Vidhya Lakshmi, G. A. Suganya Josephine, Paramasivan T. Perumal*
R 1
N
H 2
NC
NC
HN
NC
N
R
CN
H
O
N
N
R1
NC
N
R
CN
O
O
N
NC
NC
H N 2
+
CN
CN
NEt ethanol,
3
reflux R1 N
NC N
N
R
O
O
R 1
N
H 2
HN
O
NC
N
CN
H
O
N
N
N
H 2
( or )
HN
( or )
R
H
R2CHO R2 Lewis acid-assisted olefin cross-metathesis reaction: an efficient approach for the synthesis of glycosidicpyrroloquinolinone
based novel building blocks of camptothecin and evaluation of their antitumor activity
Lingaiah Nagarapu*, Hanmant K. Gaikwad, Rajashaker Bantu, Sheeba Rani Manikonda, C. Ganesh Kumar, Sujitha Pombala
N
O
N
+ H
O
R1 R2
R3
Ti(O i Pr)4 30 mol %
[Cl2(Im)(PCy3)Ru=CHPh],
10 mol %, CH2Cl2, 40 °C.
The synthesis of antitumor active glycosidic-pyrroloquinolinone based novel building blocks of camptothecin via Lewis acid-assisted olefin crossmetathesis
reaction.
N
N
O
H
R1
O
R2
R3
O
NC
CN
N
N
pp 1287–1291
Synthesis of a,a-dideutero-b-amino esters pp 1292–1295
S. Chandrasekhar*, Mrunal Pendke, Chandrashekar Muththe, Srirama Murthy Akondi, Prathama S. Mainkar
R
N R'
H
CD 3CN
LDA
THF
-78 °C
R
HN R'
R=Ar,Alkyl;R'=Bn,RorS
CN
D D
Ph
H 2SO 4
CH 3OH
R
HN R'
COOCH 3
D D

A study of monoelectronic reduction of Artemisinin pp 1296–1299
Maria Luisa Navacchia, Massimo L. Capobianco, Mila D’Angelantonio, Giancarlo Marconi*
O O
O
H
O
O
ART
H
e
H2O/EtOH
- solv
O
O
OH
O ACID
A novel reaction mechanism for the formation of deoxyanthocyanidins pp 1300–1303
André Sousa, Nuno Mateus, Victor de Freitas*
Cinnamic aldehydes:
R= H. coniferaldehyde
R= OCH3. sinapaldehyde
HO
H3CO
R
3'
2'
4'
OH
HO
7
8
A
8a
O
C
1'
2
B
6'
5'
OCH3 6
5
4a
4
3
H
OH H
Deoxyanthocyanidins:
R= H. 3-deoxypeonidin
R= OCH3. 3-deoxymalvidin
*Corresponding author
Supplementary data available via SciVerse ScienceDirect
Contents / Tetrahedron Letters 53 (2012) 1193–1199 1199
R
O
CH CH C
H
(Intermediary compounds)
0.04
0.03
A
0.02
0.01
+H +
HO
487nm
H3CO
0
350 400 450 500 550 600
Wavelength (nm)
3-deoxypeonidin
R
OH
CH CH C
HO OH
H
OH
phloroglucinol
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