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Fukuyama Group - Group Meeting Problems 07/17/2011

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1<br />

2<br />

3<br />

4<br />

O<br />

O<br />

Ph<br />

<strong>Fukuyama</strong> <strong>Group</strong> - <strong>Group</strong> <strong>Meeting</strong> <strong>Problems</strong><br />

<strong>07</strong>/<strong>17</strong>/<strong>2011</strong><br />

O<br />

H<br />

Me<br />

PhHN<br />

O<br />

+<br />

Me<br />

N<br />

PhI<br />

BF 4<br />

CO 2H<br />

O<br />

OH<br />

KOCEt 3 (3 eq)<br />

THF<br />

–78 °C to rt<br />

TFAA (3 eq*)<br />

AcOEt<br />

0 °C to rt<br />

74%<br />

87%<br />

(* theoretically 2 eq)<br />

SiMe 3 BocNHOH (2.5 eq)<br />

NaIO 4 (2.5 eq)<br />

MeOH/ H 2O<br />

20 °C<br />

52%<br />

[Fe 2(CO) 9]* (2 eq)<br />

benzene<br />

95 °C;<br />

DBU (20 eq)<br />

95 °C<br />

51%<br />

* low yield under basic condition<br />

Ph 3PEtBr<br />

n-BuLi, THF<br />

–20 °C to rt;<br />

AcOH, 80 °C<br />

87%<br />

Ph<br />

Me<br />

O<br />

N<br />

Me<br />

O O<br />

E. M. Carreira et al., Angew. Chem. Int. Ed., 50, 2962 (<strong>2011</strong>)<br />

Dy(OTf) 3<br />

CH 3CN, 80 °C<br />

90%<br />

J. R. Alaniz et al., Angew. Chem. Int. Ed., 50, 7167 (<strong>2011</strong>)<br />

OsO 4, NMO<br />

THF/ t-BuOH/ H 2O<br />

20 °C<br />

82%<br />

CF 3<br />

M. Kawase et al., Org. Lett., 12, 4776 (2010)<br />

SmI 2<br />

THF<br />

–78 °C<br />

60%<br />

O<br />

PhN<br />

HO<br />

HO<br />

Boc<br />

Y. Landais et al., Org. Lett., 10, 4195 (2008)<br />

H<br />

NH<br />

OH<br />

OH<br />

* OH<br />

NBoc<br />

OH<br />

1<br />

H<br />

* 1 stereochemistry<br />

not determined


1<br />

MeO<br />

2<br />

3<br />

4<br />

H<br />

HO<br />

H<br />

O<br />

<strong>Fukuyama</strong> <strong>Group</strong> - <strong>Group</strong> <strong>Meeting</strong> <strong>Problems</strong><br />

<strong>07</strong>/24/<strong>2011</strong><br />

H H O H<br />

O<br />

O<br />

LTA<br />

N 2<br />

CHCl 3<br />

-40 °C<br />

61%<br />

BHT, PhH<br />

235 ºC, 88%<br />

O<br />

Ph Ph NIS (2.5 eq)<br />

O O<br />

H2O (5.0 eq)<br />

MeCN<br />

–40 to 0 °C<br />

N<br />

62%*<br />

Tricyclic Compound<br />

(C <strong>17</strong>H 24O 3)<br />

(*18% other diastereomixture)<br />

1) MeMgBr, CuBr•Me 2S<br />

Me 2S, THF, –20 ºC<br />

66%, 14:1 dr<br />

2) TMSCHN 2<br />

MeOH/PhH, rt, 93%<br />

[Rh(OCOC 7H 15) 2] 2 (cat.)<br />

DMAD<br />

CH 2Cl 2<br />

rt<br />

70%<br />

1) DDQ<br />

MeCN-H 2O (10:1)<br />

60 °C<br />

58% (36% SM)<br />

2) NaH 2PO 4, NaClO 2<br />

2-methyl-2-butene<br />

t-BuOH-H 2O (5:1), rt<br />

92%<br />

BHT, PhH<br />

120 ºC, 96%<br />

MeO<br />

H<br />

Me<br />

H<br />

O<br />

CO 2Me<br />

M. L. Snapper et al., Org. Lett., 3, 2819 (2001)<br />

MeO 2C<br />

MeO 2C<br />

O<br />

O<br />

N<br />

A. Padwa et al., Tetrahedron Lett., 34, 7853 (1993)<br />

1) CrO 3<br />

H 2SO 4/H 2O/acetone<br />

rt, 96%<br />

2) OsO 4, THF<br />

rt, 79%<br />

3) p-TsOH⋅H 2O<br />

toluene, reflux<br />

85%<br />

H<br />

O<br />

O O O<br />

T. R. R. Pettus et al., J. Am. Chem. Soc., 133, 1603 (<strong>2011</strong>)<br />

CAN<br />

MeCN-H 2O (1:1)<br />

rt;<br />

K 2CO 3<br />

80%<br />

O O<br />

Y. Kita et al., Angew. Chem. Int. Ed., 44, 734 (2005)<br />

I<br />

O


1<br />

2<br />

3<br />

4<br />

O<br />

O<br />

TBSO<br />

N 2<br />

O<br />

<strong>Fukuyama</strong> <strong>Group</strong> - <strong>Group</strong> <strong>Meeting</strong> <strong>Problems</strong><br />

<strong>07</strong>/31/<strong>2011</strong><br />

N<br />

Me<br />

N<br />

H<br />

*<br />

OH<br />

OH<br />

* : Diastereomixture<br />

O<br />

O<br />

Br<br />

MeO2C N<br />

Me<br />

I<br />

OH<br />

1) allyl alcohol<br />

Rh 2(OAc) 4<br />

CH 2Cl 2, rt<br />

2) xylenes<br />

reflux<br />

85% (2 steps)<br />

NMe<br />

OAc<br />

Pd(PPh 3) 4, i-Pr 2NH<br />

microwave<br />

benzene<br />

160 °C<br />

60%<br />

SmI 2, HMPA<br />

i-PrOH<br />

THF, –35 °C<br />

99%<br />

TFA, rt<br />

61%<br />

3) H(OH)NMe⋅HCl<br />

pyridine, MeOH<br />

reflux<br />

O<br />

MeN<br />

4) imidazole⋅HCl<br />

H<br />

EtOH, reflux<br />

O<br />

81% (2 steps) N<br />

Me<br />

J. L. Wood et al., Tetrahedron, 66, 6647 (2010)<br />

S. Blechert et al., J. Am. Chem. Soc., 126, 3534 (2004)<br />

1) DMP<br />

CH 2Cl 2, rt<br />

77%<br />

2) cat. RuCl 3, NaIO 4<br />

CCl 4-CH 3CN-H 2O<br />

50%<br />

N<br />

H<br />

O<br />

O<br />

O<br />

H<br />

O<br />

O<br />

NMe<br />

O O<br />

CO 2Me<br />

J. Suffert et al., Angew. Chem. Int. Ed., 50, 3285 (<strong>2011</strong>)<br />

1) CsF, PhN(Tf) 2<br />

DME<br />

2) Pd(OAc) 2, PPh 3<br />

HCO 2H, DMF<br />

87% (2 steps)<br />

LDA<br />

THF, –78 °C;<br />

MeI<br />

67%<br />

Me<br />

O<br />

NMe<br />

Y. Landais et al., Org. Lett., 10, 4441 (2008)

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