Tetrahedron Letters Vol. 54, Issue 51, 2013

Contents

COMMUNICATIONS

The development of N-aryl trifluoroacetimidate-based benzyl and allyl protecting group reagents pp 6983–6985

Sinele B. Tsabedze, Daniel E. K. Kabotso, Nicola L. B. Pohl*

F3C OR

N

NO2

crystalline

acidR'OH R'OR

R = benzylor allyl

Nano ceria catalyzed synthesis of substituted benzimidazole, benzothiazole, and benzoxazole in aqueous media pp 6986–6990

Radheshyam Shelkar, Sachin Sarode, Jayashree Nagarkar*

An InBr3 catalyzed one-pot three-component synthesis of functionalized spirodihydrofuran oxindoles viaintramolecular alkyne carbonyl metathesis

pp 6991–6994

I. R. Siddiqui*, Rahila, Shayna Shamim, Pragati Rai, Shireen, Malik A. Waseem, Afaf A. H. Abumhdi

N

O

OH R

InBr3, Et3N

22h, rt

R'Br

O

CH3CN N O

OR'

R

O

1 2(a-d) 3(a-c) 5 (a-l)

6975

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Stemona-amines C–E, new alkaloids from Stemona tuberosa pp 6995–6998

Yukio Hitotsuyanagi, Genta Shigemori, Haruhiko Fukaya, Maho Hikita, Shu Zhu, Katsuko Komatsu, Koichi Takeya*

Stemona-amine C Stemona-amine EStemona-amine D

N

O

O

O

H

HO OH

H

O

H

ONO

O

OH

HH

H

H HHO

HON

O

O

OH

HH

H

H HHO

H

Synthesis of rapamycin glycoconjugates via a CuAAC-based approach pp 6999–7003

Lisa Moni, Alberto Marra, Jerauld S. Skotnicki, Frank E. Koehn, Magid Abou-Gharbia*, Alessandro Dondoni*

Catalytic asymmetric bromolactonization reactions using (DHQD)2PHAL-benzoic acid combinations pp 7004–7008

Alan Armstrong*, D. Christopher Braddock*, Alexander X. Jones, Stacy Clark

Systematic survey of positive chlorine sources in the asymmetric Appel reaction: oxalyl chloride as a new phosphineactivator

pp 7009–7012

Kamalraj V. Rajendran, Lorna Kennedy, Cormac T. O’Connor, Enda Bergin, Declan G. Gilheany*

-78 °CMenthol

P

R2R1R3

Cl X

oxalyl chloride

Positive ChlorineSources

CPS

P

R2R1R3 P

R2R1 R3

OMen

DAPS

ClP

R1R3R2

OArbuzov

or

(new and versatilephosphine activator)

6976 Contents / Tetrahedron Letters 54 (2013) 6975–6981

A robust Ru-PNNP catalyst system for the asymmetric hydrogenation of a,b-unsaturated ketones to allylic alcohol pp 7013–7016

Sheng-Mei Lu*, Qiang Gao, Jun Li, Yan Liu, Can Li

O

N N

O

PPh2 Ph2P

L1

R1

O

R2 R1

OH

R2

[Ru(cymene)Cl2]2 / L1EtOH, H2 (10 bar)6 h, LiOH H2O1 2

R1 = aryl, heteroaryl, alkyl, R2 = aryl, alkyl up to 98% yield and 98% ee

Reinvestigation of palladium-catalyzed allylation of the monoacetate of 4-cyclopentene-1,3-diol and synthesisof the coronafacic acid ethyl ester

pp 7017–7020

Wataru Kinouchi, Yusuke Kosaki, Yuichi Kobayashi*

An efficient and convenient synthesis of unsymmetrical disulfides from thioacetates pp 7021–7023

Slawomir Lach, Sebastian Demkowicz, Dariusz Witt*

OP

O S

S S R1 SR2

OR1 S S R2

MeONa (2equiv.)MeOH, rt, 15-30 minorBuNH2 (4 equiv.)MeOH, rt, 15-30 min1 2 3

+

A novel strategy for developing yellow diarylethenes based on acid stimulus pp 7024–7028

Chunhong Zheng, Shouzhi Pu*, Gang Liu, Bing Chen

Contents / Tetrahedron Letters 54 (2013) 6975–6981 6977

Improved synthesis of (R)-7-hydroxycarvone from (S)-a-pinene pp 7029–7030

Yuki Egoshi, Ryosuke Kondo, Yukiko Yoshimoto, Toru Sugiyama, Toyonobu Usuki*

Effective synthesis of cyclic carbonates from carbon dioxide and epoxides by phosphonium iodides as catalysts inalcoholic solvents

pp 7031–7034

Naoto Aoyagi, Yoshio Furusho, Takeshi Endo*

PPh3•HI (5 mol%)

4% yield 93% yield26% yield<<<

OO

CO2+O O

O

O

MeOH < i-PrOHEtOH

1 atmProtic solvent , 25 °C

Immobilization of Ru(III) complex on silica: a heterogenized catalyst for selective oxidation of alcohols in waterat room temperature

pp 7035–7039

S. Ganesamoorthy, M. Muthu Tamizh, K. Shanmugasundaram, R. Karvembu*

OH

O

O

O

OH

O

OOH

Si

H2N

SiH2N

O

RuH3CCN

O

O

O

O

RuH3CCN

O

O

O

O

PF6+ _

PF6+ _SiO2 H5IO6

H2O27 C

O

R1 R2

OH

R1 R2

Isolation of key intermediates during formation of oolongtheanins pp 7040–7043

Sayumi Hirose, Kaoru Tomatsu, Emiko Yanase*

OH

OH

HO

OH

O

OG

O

OO

OH

H

HO

OH

O

OG

EGCg O

OH

H OH

HO

O

OH

OH

HO

OH

O

OG

HO

OH

O

OG

HO

OH

O

OG

O

O

OH

H

OH

OH

HO

OH

O

OG

6978 Contents / Tetrahedron Letters 54 (2013) 6975–6981

An expedient domino three-component [3+2]-cycloaddition/annulation protocol: regio- and stereoselective assemblyof novel polycyclic hybrid heterocycles with five contiguous stereocentres

pp 7044–7048

Shanmugavel Uma Maheswari, Subbu Perumal*

N

O

Ar

OO

H3CHN COOH

S

NH

COOH(or)

toluenereflux, 10-12 h

N

O

N

ArH

R1HOH

16 examples81-90 % yieldR1 = Me; R2 = H (or)R1 and R2 = -CH2-S-CH2-

R2

Monomeric and dimeric red/NIR-fluorescent dipyrrin–germanium complexes: facile monomer–dimer interconversiondriven by acid/base additions

pp 7049–7052

Masaki Yamamura, Hiroyuki Takizawa, Naoya Sakamoto, Tatsuya Nabeshima*

An unusual involvement of NaIO4 in the acetylation of bisphenol during attempted oxidative acetylation pp 7053–7055

Deepak Singh, Pradeep T. Deota*

OHHO

R2R1

NaIO4, Ac2O,

75°C

OAcAcO

R2R1

OO

OAcR2R1

OAc

ExpectedIsolated

R1, R2 = H, alkyl groups.

A novel and convenient strategy for the synthesis of phthalazines from an aryne precursor pp 7056–7058

Hassen Bel Abed, Omprakash Bande, Oscar Mammoliti, Guy Van Lommen, Piet Herdewijn*

Contents / Tetrahedron Letters 54 (2013) 6975–6981 6979

Early introduction of the amino group to the C27–C35 building block of Eribulin pp 7059–7061

Alena Rudolph, Dino Alberico, Robert Jordan, Ming Pan, Fabio E. S. Souza, Boris Gorin*

Ar = Ph, p-tolyl

O

MeOSO2Ar

CHOO

BocN

O

O

MeOOH

H2N

O

OO

O

O

O

O

C27

C34C35

Parallel synthesis of bis-oxazole peptidomimetics pp 7062–7064

Siva Murru, Colette T. Dooley, Adel Nefzi*

NHBocNHO

O

O

R Solidphase

5 building blocks 25 bis-oxazole peptidomimetics

NHBocHO

O

RNH2

O

O

OH+

HN

NH2N

O

O

R

NH2NO

O

R'R = Leu, ProVal, Phe

Tyr

4 steps

Expedient synthesis of novel b-ketoesters from the Mizoroki–Heck coupling of ethyl 3-ethoxyacrylate with aryland pyridyl halides

pp 7065–7068

Jeffrey T. Kohrt*, Ed Conn, Robert Maguire, Stephen W. Wright, Robert Singer

EtO

O

OEt

Het/Ar-X

6% Pd (PtBu3)2DCMA, 3 eq. LiCl110 oC, Dioxane

Ar/Het

O

OEt

Ar/Het

O

OEt

O

acid

HydrolysisOEt

Iodine-catalyzed cycloalkenylation of dihydroquinolines and arylamines through a reaction with cyclic ketonesunder neat conditions

pp 7069–7073

Jean Fotie*, Suraj K. Ayer, Binit S. Poudel, Carolyn S. Reid

NH

+NH

6a: n = 2 (61%)6b: n = 1 (58%)

5 eqvn = 1 or 2

O

(CH2)n

(CH2)n

(CH2)n

I2 (5% mol)

160°C, 72 hneat, air

6980 Contents / Tetrahedron Letters 54 (2013) 6975–6981

Sodium carbonate mediated regioselective synthesis of novel N-(hydroxyalkyl)cinnamamides pp 7074–7077

Parul Garg, Marilyn Daisy Milton*

+

n = 0,1

OMe

O

R1 Na2CO3

MeOH, 80 °C1.25-8 h

20 examplesupto 99% isolated yields

NH2 OHn

HN

O

OHn

R4

R4R3R2

R3R2

R1

Cesium carbonate mediated aryl triflate esters’ deprotection pp 7078–7079

Alice E. Green, Vangelis Agouridas*, Eric Deniau

Base mediated deprotection strategies for trifluoroethyl (TFE) ethers, a new alcohol protecting group pp 7080–7082

Qingliang Yang, Jon T. Njardarson*

RO

CF3

LDAR

OF

F

Li

MoOPHR

OF

F

OR OH

H2OR

OF

Fcat.

OsO4

*Corresponding authorSupplementary data available via ScienceDirect

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Contents / Tetrahedron Letters 54 (2013) 6975–6981 6981