Tetrahedron Letters Vol. 54, Issue 18, 2013

Contents

COMMUNICATIONS

Rhodium catalyzed hydroformylation with formaldehyde and an external H2-source pp 2209–2211

Marcus Uhlemann, Stephan Doerfelt, Armin Börner*

HCHO, Rh-cat.R + H2

R

CHO

R+ isomerized

olefin+

R

OHC

l

b

An efficient protocol for the preparation of amides by copper-catalyzed reactions between nitriles and aminesin water

pp 2212–2216

Xiaoya Li, Zhengkai Li, Hang Deng, Xiangge Zhou*

10 mol% Cu(OAc)2 / L (20 mol%)

100 °C, 18h, H2OR N

H

O

+ R'R CN

NH

COOHL =

NH2R'

41 examples with yields up to 90%

Deprotection of 1,3-oxathiolanes to ketones promoted by base pp 2217–2220

Biao Du, Changchun Yuan, Langzhong Zhang, Li Yang, Bo Liu*

LTMP (5.0 equiv.)R1

SOR2 R1 R2

O

THF17 examples72%-89% yield

OPG (PG= -TBS and -MOM)

1,3-Dithianes Inert to LTMPDimethylketals 1,3-Dioxolanes and

2203

Contents lists available at SciVerse ScienceDirect

Tetrahedron Letters

journal homepage: www.elsevier .com/ locate/ tet le t

Ligand-free palladium-catalyzed intramolecular arylation of chromones: an expedient synthesis of1-benzopyrano[3,2-c]quinolines

pp 2221–2225

Jaydip Ghosh, Pritam Biswas, Sourav Maiti, Tapas Sarkar, Michael G. B. Drew, Chandrakanta Bandyopadhyay*

O

O

CHO

NH2X

ZR1

R2NCO

O

NR1

O

R3

N O

R2

H

Z

(i) R3CO2H/StirringRT/30 min

(ii) PdCl2/KOAc/DMF100-110 oC/2 h

Efficient and scalable synthesis of ketones via nucleophilic Grignard addition to nitriles using continuous flowchemistry

pp 2226–2230

Carlos Mateos*, Juan A. Rincón, José Villanueva

Spiroaminal model systems of the marineosins with final step pyrrole incorporation pp 2231–2234

Joseph D. Panarese, Leah C. Konkol, Cynthia B. Berry, Brittney S. Bates, Leslie N. Aldrich, Craig W. Lindsley*

HO2CCO2H

OH

NH

O

MeO

O N

MeO

O HN

Tf2O, CH2Cl2pyrrole

36%

5 steps

26% overall

N

OMe

HN

O

HN

9% overallMarineosin A

An acetylene zipper—Sonogashira reaction sequence for the efficient synthesis of conjugated arylalkadiynols pp 2235–2238

Alexandra E. Kulyashova, Viktor N. Sorokoumov, Vladimir V. Popik, Irina A. Balova*

1. LAETA

2. H2OOH

RR H

ROH

R

Pd0/Cu+1Ar

ROH

R

H3C n n+1 n+1

ArI

32−87%

2204 Contents / Tetrahedron Letters 54 (2013) 2203–2208

Novel pathway for the synthesis of arylpropionamide-derived selective androgen receptor modulator (SARM)metabolites of andarine and ostarine

pp 2239–2242

Katharina M. Schragl, Guro Forsdahl, Guenter Gmeiner, Valentin S. Enev*, Peter Gaertner*

A highly regioselective, protecting group controlled, synthesis of bicyclic compounds via Pd-catalysedintramolecular cyclisations

pp 2243–2246

Gordana Tasic, Jelena Randjelovic, Nikola Vusurovic, Veselin Maslak, Suren Husinec, Vladimir Savic*

NO

IROMe

N

TBDMSO

O

MePd(OAc)2

PPh3

toluene110 oC15 h

Pd(OAc)2

PPh3

toluene

110 oC15 h

O

O NMe

R = TBDMSR = H

Et3N Et3N

73%

ONMe

+1 : 1.3

75%

Insight into the chemistry of cycloaddition between a-ketol oxylipin and epinephrine: isolation and structureelucidation of a new reaction product

pp 2247–2250

Kenji Kai, Yukie Oba, Ryota Akaike, Ariaki Murata, Toshio Nishikawa, Naoharu Watanabe*

O

COOHOH

OH

OHNH

OHN

O

O

HO

O

COOH

OHOH

N

HO

O

O

O

OHCOOH

Hα-ketol oxylipin

epinephrinenew reaction product KE

Expeditious synthesis of chiral 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazines pp 2251–2254

Subhendu Bhowmik, Anil K. S. Kumar, Sanjay Batra*

R

BocHN

O NH2

NNH

RO*

i. EDCI.HCl, NMM,CH2Cl2, -15 oC, 1 h,ii. HCl: AcOH (1:9),rt, 12 h,iii. Aq. NaHCO3 , pH= 7.0, reflux, 3 h

one-pot

O

OH

+

*

13 examples77-92%

LiAlH4, dry THF,70 oC, 1 h

NNH

R

*

6 examples92-96%

Contents / Tetrahedron Letters 54 (2013) 2203–2208 2205

RCM strategy-based entry into new crown ether/polyether macrocyclic systems derived from hydroxybenzaldehydes

pp 2255–2260

Naveen, Ramarao Parella, Srinivasarao Arulananda Babu*

O

O

O

O

O OO O

OOO

O O

OOO

O O

OO

O

O O

OO

O OH

CaF2 catalyzed SN2 type chlorodehydroxylation of chiral secondary alcohols with thionyl chloride: a practical andconvenient approach for the preparation of optically active chloroalkanes

pp 2261–2263

Junjie Zhang, Huanxia Wang, Yun Ma, Youming Wang*, Zhenghong Zhou*, Chuchi Tang

R R1

OH SOCl2 (1.1 equiv)/CaF2 (10 mol%)

R R1

Cl

* *Inversion of configuration

CaF2 has been proven to be an efficient catalyst for the chlorodehydroxylation of chiral secondary alcohols with thionyl chloride, providing the corresponding chloroalkanes ingood yield with high optical purity with inversion of the original configuration of the alcohol.

A solvent-free Diels–Alder cycloaddition of piperine on silica gel: synthesis of dimeric amide alkaloid from theroots of Piper nigrum

pp 2264–2266

Kun Wei*, Shunxin Wang, Zhimeng Liu, Yu Du, Xuebo Shi, Ting Qi, Shen Ji

N

O

O

O

O

O

O

ON

O

ON

1 2

silica gel

solvent-free

Sinulanorcembranolide A, a novel norcembranoidal diterpene from the octocoral Sinularia gaweli pp 2267–2270

Wei-Hsuan Yen, Yin-Di Su, Yu-Chia Chang, Yu-Hsin Chen, Yung-Husan Chen, Chang-Feng Dai, Zhi-Hong Wen,Jui-Hsin Su*, Ping-Jyun Sung*

O

OH

HO

O

OHH H

Sinularia gaweli Sinulanorcembranolide A

2206 Contents / Tetrahedron Letters 54 (2013) 2203–2208

A facile synthesis of 2,3,6,7-tetrabromonaphthalene diimides toward new p-extended naphthalene diimides pp 2271–2273

Yunbin Hu, Zhongli Wang, Xiaodi Yang, Zheng Zhao, Wenjie Han, Wei Yuan, Hongxiang Li, Xike Gao*, Daoben Zhu

O

O

OO

OO

Br

BrBr

Br 2) PBr3

N

N

OO

OO

Br

BrBr

Br

C8H17

C8H17

NKS

KS CN

THF, 50 °C

N

N

OO

OO

C8H17

C8H17

S

SS

SNN CNNC

1) n-C8H17NH2CH2Cl2

(72% yield) (64% yield)2 1

A 2,3,6,7-tetrabromonaphthalene diimide (2) was readily synthesized in high yield from 2,3,6,7-tetrabromonaphthalene dianhydride by an improveddehydrohalogenation-based imidization reaction. The further nucleophilic aromatic substitution (SNAr) reaction of 2 with potassium cyanocarbonimi-dodithioate afforded a new p-extended naphthalene diimide (1), which exhibits n-type behavior in organic transistors and interesting response toF) among halide anions in solutions.

Synthesis of a maradolipid without using protecting groups pp 2274–2276

René Csuk*, Andrea Schultheiß, Sven Sommerwerk, Ralph Kluge

An efficient metal-free synthesis of organic disulfides from thiocyanates using poly-ionic resin hydroxidein aqueous medium

pp 2277–2281

Debasish Sengupta, Basudeb Basu*

R SCNor

Ar

O

SCN

Amberlyst® A-26 (OH)

Water / 60 - 80 oC

R SS R

or

Ar

O

S

2

(74 - 92%)

(16 examples)

Metal-free, on-water procedureand superior to using other

homogeneous bases

*Corresponding authorSupplementary data available via SciVerse ScienceDirect

Contents / Tetrahedron Letters 54 (2013) 2203–2208 2207

Abstracted/indexed in: AGRICOLA, Beilstein, BIOSIS Previews, CAB Abstracts, Chemical Abstracts, Chemical Engineering andBiotechnology Abstracts, Current Biotechnology Abstracts, Current Contents: Life Sciences, Current Contents: Physical,Chemical and Earth Sciences, Current Contents Search, Derwent Drug File, Ei Compendex, EMBASE/Excerpta Medica, Medline,PASCAL, Research Alert, Science Citation Index, SciSearch. Also covered in the abstract and citation database SciVerse Scopus�.Full text available on SciVerse ScienceDirect�

Available online at www.sciencedirect.com

ISSN 0040-4039

2208 Contents / Tetrahedron Letters 54 (2013) 2203–2208