References and Notes
1 Inouye SE.
Tsuruoka Y.
Ito T.
Niida T.
Tetrahedron
1968,
24:
2125
2 Somsak L.
Nagya V.
Hadady Z.
Docsa T.
Gergely P.
Curr. Pharm.
Des.
2003,
9:
1177
3 Weiss M.
Hettmer S.
Smith P.
Ladish S.
Cancer Res.
2003,
63:
3654
4 Greimel P.
Spreitz J.
Stutz AE.
Wrodnigg TM.
Curr. Topics Med.
Chem.
2003,
3:
513
5 Butters TD.
Dwek RA.
Platt FM.
Chem.
Rev.
2000,
100:
4683
6 Ficher PB.
Collin M.
Karlsson GB.
Lames W.
Butters TD.
Davis SJ.
Gordon S.
Dwek RA.
Platt FM.
J.
Virol.
1995,
69:
5791
7 Fischl MA.
Resnick L.
Cooms R.
Kremer AB.
Pottage JC.
Fass RJ.
Fife KH.
Powderly WG.
Collier AC.
Aspinalli RL.
J. Acquir. Immune Defic.
1994,
7:
139
8 Cox T.
Lachmann R.
Hollak C.
Aerts J.
Weely S.
Hrebicek M.
Platt F.
Butters T.
Dwek R.
Moyses C.
Gow I.
Elstein D.
Zimran A.
Lancet
2000,
355:
1481
9a Afarinkia K.
Bahar A.
Tetrahedron: Asymmetry
2005,
16:
1239
9b Pearson MSM.
Allaimat MM.
Fargeas V.
Lebreton J.
Eur.
J. Org. Chem.
2005,
2159
9c Asano N.
Oseki K.
Kizu H.
Matsui K.
J. Med. Chem.
1994,
37:
3701
9d O’Brien JL.
Tosin M.
Murphy PV.
Org. Lett.
2001,
3:
3353
9e Spreidz JS.
Stutz AE.
Wrodnigg TM.
Carbohydr. Res.
2002,
337:
183 ; and references cited therein
9f Haukaas MH.
O’Doherty GA.
Org.
Lett.
2001,
3:
401
9g Ruiz M.
Ojea V.
Ruanova TM.
Quintela JM.
Tetrahedron: Asymmetry
2002,
13:
795
9h Takahata H.
Banba Y.
Sasatani M.
Nemoto H.
Kato A.
Adachi I.
Tetrahedron
2004,
60:
8199 ; and literature cited therein
9i Guaragna A.
D’Errico S.
D’Alonzo D.
Pedatella S.
Palumbo G.
Org. Lett.
2007,
9:
3473
9j Bagal SK.
Davies SG.
Lee JA.
Roberts PM.
Russell AJ.
Scott PM.
Thomson JE.
Org.
Lett.
2010,
12:
136
9k Palyam N.
Majewski M.
J. Org. Chem.
2009,
74:
4390
10a Schmidt U.
Meyer R.
Leitenberger V.
Stabler F.
Lieberknecht A.
Synthesis
1991,
409
10b Schmidt U.
Meyer R.
Leitenberger V.
Lieberknecht A.
Griesser H.
Chem.
Commun.
1991,
275
11 Cram DJ.
Kopecky KR.
J. Am. Chem. Soc.
1959,
81:
2748
12a Martin SF.
Li W.
J. Org. Chem.
1989,
54:
6129
12b Amouroux R.
Ejjiyar S.
Chastrette M.
Tetrahedron Lett.
1986,
27:
1035
12c Asami M.
Kimura R.
Chem. Lett.
1985,
4:
1221
12d Uenishi J.
Tomozane H.
Yamato M.
13a Cherest M.
Felkin H.
Prudent N.
Tetrahedron Lett.
1968,
9:
2119
13b Cherest M.
Felkin H.
Tetrahedron Lett.
1968,
2205
13c Anh NT.
Eisenstein OE.
Nouv.
J. Chim.
1977,
1:
61
13d Anh NT.
Top. Curr. Chem.
1980,
88:
145
14 Wipf P.
Xu W.
Tetrahedron Lett.
1994,
35:
5197
15 The structure of Garner’s
aldehyde is shown in Figure
[²
Figure 2
16 Murakami T.
Furusawa K.
Tetrahedron
2002,
58:
9257
17
Procedure for
the Synthesis of 5 : To a 250-mL flame-dried flask loaded with
zirconocene chloride hydride (4.63 g, 18.0 mmol) under argon was
added anhyd CH2 Cl2 (35 mL). The resulting
suspension was cooled to 0 ˚C after which 7 (3.06 g,
18.0 mmol) was added dropwise. The mixture was then stirred at r.t.
until the suspension had fully dissolved forming a yellow solution
(1 h). The solution was cooled to -30 ˚C after
which diethylzinc (16.5 mL, 18.0 mmol, 1.1 M in toluene) was added
dropwise. After 15 min of stirring aldehyde 6 (3.95
g, 15.0 mmol) was added as a CH2 Cl2 solution
(20 mL) via cannula. After 15 min of further stirring at -30 ˚C,
the solution was allowed to warm to 0 ˚C and the orange
mixture was stirred overnight. The reaction mixture was diluted
with CH2 Cl2 (80 mL) followed by addition of sodium
potassium tartrate (15 g) and H2 O (30 mL, added slowly).
The resulting mixture was stirred for 45 min and filtered through
a pad of celite. The phases were separated and the aqueous phase
was extracted with CH2 Cl2 (3 × 40 mL).
The organic layer was dried over Na2 SO4 , and concentrated
to give a crude product, which was chromatog-raphed on silica gel
(10% EtOAc in cyclohexane) to give compound 5 (4.96
g, 76%) as a colorless oil; [α]D
²5 -12.1
(c = 2.0, CH2 Cl2 ). ¹ H
NMR (400 MHz, DMSO): δ = 7.31-7.40 (m,
5 H), 5.81 (dt, J = 15.2, 4.0
Hz, 1 H), 5.65 (dd, J = 15.2, 5.2
Hz, 1 H), 5.16 (d, J = 4.8 Hz,
1 H), 5.01-5.10 (m, 2 H), 4.02-4.17 (m, 4 H),
3.46-3.53 (m, 1 H), 3.19 (t, J = 8.8
Hz, 1 H), 1.51 (s, 3 H), 1.44 (s, 3 H), 0.85 (s, 9 H), 0.02 (s,
6 H). ¹³ C NMR (100 MHz, DMSO): δ = 152.0,
137.2, 131.4, 128.8, 128.7, 128.3, 128.0, 93.8, 77.2, 71.2, 66.1,
62.9, 46.7, 26.3, 26.2, 24.3, 18.4, -4.8. IR: 3436, 2929,
1710, 1411 cm-¹ . LRMS (EI, 70 eV): m /z (%) = 420
(8) [M+ - Me], 91
(100). HRMS (EI): m /z [M+ - Me] calcd
for C22 H34 NO5 Si: 420.2206; found:
420.2201.
18a Gao Y.
Hanson RM.
Klunder JM.
Ko SY.
Masamune H.
Sharpless KB.
J.
Am. Chem. Soc.
1987,
109:
5765
18b Johnson RA.
Sharpless KB. In
Catalytic Asymmetric Synthesis
Ojima I.
Wiley Publishers;
New
York:
1993.
p.103-105
19 Setoi H.
Takeno H.
Hashimoto M.
Tetrahedron
Lett.
1985,
26:
4617
20 Lindstrom UM.
Somfai P.
Tetrahedron Lett.
1998,
39:
7173
21a Fleet GWJ.
Carpenter NM.
Petursson S.
Ramsden NG.
Tetrahedron Lett.
1990,
31:
409
21b Ermert P.
Vasella A.
Helv. Chim. Acta
1991,
74:
2043
21c Ilida H.
Yamazaki N.
Kibayashi C.
J.
Org. Chem.
1987,
52:
3337
