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284
R. A. Fernandes, R. Brückner
LETTER
Curini, M.; Marcotullio, M. C.; Rosati, O. J. Org. Chem.
1990, 55, 311. (d) Checcherelli, P.; Curini, M.; Marcotullio,
M. C.; Rosati, O.; Wenkert, E. J. Org. Chem. 1991, 56,
7065. (e) Prestwich, G. D.; Ujváry, I. J. Labelled Comp.
Radiopharm. 2002, 2, 37.
(
(
(
(
2) (a) Bergy, M. E. J. Antibiot. 1968, 21, 454. (b) Hoeksema,
H.; Krueger, W. C. J. Antibiot. 1976, 29, 704.
3) Iwai, Y.; Kora, A.; Takahashi, Y.; Hayashi, T.; Awaya, J.;
Masuma, R.; Oiwa, R.; Omura, S. J. Antibiot. 1978, 31, 959.
4) Omura, S.; Tanaka, H.; Okada, Y.; Marumo, H. J. Chem.
Soc., Chem. Commun. 1976, 320.
(16) Kapferer, T.; Brückner, R. unpublished results.
(17) Giles, R. G. F.; Mitchell, P. R. K.; Roos, G. H. P.; Strümpfer,
J. M. M. J. Chem. Soc., Perkin Trans. 1 1981, 2091.
(18) (a) Tsuji, J.; Kiji, J.; Imamura, S.; Morikawa, M. J. Am.
Chem. Soc. 1964, 86, 4350. (b) Murahashi, S.-I.; Imada, Y.;
Taniguchi, Y.; Higashiura, S. J. Org. Chem. 1993, 58, 1538.
(19) (a) Jung, M. E.; Hagenah, J. A. J. Org. Chem. 1987, 52,
1889. (b) Kitani, Y.; Morita, A.; Kumamoto, T.; Ishikawa,
T. Helv. Chim. Acta 2002, 85, 1186.
5) (a) Omura, S.; Tanaka, H.; Koyama, Y.; Oiwa, R.; Katagiri,
M.; Awaya, J.; Nagai, T.; Hata, T. J. Antibiot. 1974, 27, 363.
(
b) Tanaka, H.; Koyama, Y.; Nagai, T.; Marumo, H.; Omura,
S. J. Antibiot. 1975, 28, 868.
(
6) Original structure: (a) Takano, S.; Hasuda, K.; Ito, A.;
Koide, Y.; Ishii, F.; Hanada, I.; Chihara, S.; Koyami, T. J.
Antibiot. 1976, 29, 765. (b) Ogura, H.; Furuhata, K. 9th
International Congress of Heterocyclic Chemistry; Tokyo,
August 1983, Abstr. S-IV-&: 114. (c) Revised structure:
Leo, P.-M.; Morin, C.; Philouze, C. Org. Lett. 2002, 4, 2711.
7) Keller-Schlierlein, W.; Brufani, M.; Barcza, S. Helv. Chim.
Acta 1968, 51, 1257.
(20) All new compounds gave satisfactory H- and 13C NMR
spectra and provided correct combustion analyses (±0.4%).
(21) Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43,
2923.
1
(
(
8) Reviews: (a) Brimble, A. M. Pure Appl. Chem. 2000, 72,
(22) Methyl (E)-4-(1,4,5-trimethoxynaphth-2-yl)-3-butenoate
1635. (b) Brimble, A. M.; Nairn, M. R.; Prabaharan, H.
(9): NaBr (97.6 mg, 0.948 mmol, 25 mol%), Ph P (79.6 mg,
3
Tetrahedron 2000, 56, 1937.
0.303 mmol, 8 mol%), Pd (dba) CHCl (78.5 mg, 0.076
2
3
3
(
9) Moore, H. W. Science 1977, 197, 527.
mmol, 2 mol%), and i-Pr NEt (0.63 mL, 0.49 g, 3.80 mmol)
2
(
10) (a) Kraus, G. A.; Roth, B. J. Org. Chem. 1978, 43, 4923.
were added sequentially to a solution of allyl acetate 11
(1.200 g, 3.793 mmol) in MeOH (5 mL). The reaction
mixture was pressurized with CO (30 atm) in an autoclave
and stirred at 50 °C for 6 h before cooling to r.t., quenching
with H O, and extraction with CHCl (3 ꢀ 20 mL). The
(
(
b) Li, T.; Ellison, R. H. J. Am. Chem. Soc. 1978, 100, 6263.
c) Kraus, G. A.; Cho, H.; Crowley, S.; Roth, B.; Sugimoto,
H.; Prugh, S. J. Org. Chem. 1983, 48, 3439. (d) Foland, L.
D.; Decker, O. H. W.; Moore, H. W. J. Am. Chem. Soc. 1989,
2
3
111, 989. (e) Brimble, M. A.; Stuart, S. J. J. Chem. Soc.,
combined organic layers were washed twice with H O, dried
2
Perkin Trans. 1 1990, 881. (f) Kraus, G. A.; Li, J.; Gordon,
M. S.; Jensen, J. H. J. Org. Chem. 1995, 60, 1154.
(Na SO ), and concentrated. The residue was purified by
2
4
flash chromatography using cyclohexane–EtOAc (17:3 →
3:1) as an eluent to give 9 (1.001 g, 83%; 95:5 mixture with
(
(
11) Syntheses of 1 and 3: (a) Short communication: Tatsuta, K.;
Akimoto, K.; Annaka, M.; Ohno, Y.; Kinoshita, M. J.
Antibiot. 1985, 38, 680. (b) Full paper: Tatsuta, K.;
Akimoto, K.; Annaka, M.; Ohno, Y.; Kinoshita, M. Bull.
Chem. Soc. Jpn. 1985, 58, 1699. Synthesis of 3:
1
the isomeric a,b-unsaturated ester) as a yellow syrup. H
NMR (500 MHz, CDCl /TMS): d = 3.35 (dd, J = 7.1 Hz,
3
2,3
4
J2,4 = 1.5 Hz, 2-H), 3.71 (s, MeO C), 3.83, 3.93, and 3.96 (3
2
s, 3 ꢀ MeO), 6.40 (dt, J3,4 = 16.2 Hz, J3,2 = 7.1 Hz, 3-H), 6.82
(br d, J = 7.8 Hz, 6¢-H), 6.93 (s, 3¢-H), 6.96 (dt, J4,3 = 16.2
(
c) Winters, M. P.; Stranberg, M.; Moore, H. W. J. Org.
6¢,7¢
4
Chem. 1994, 59, 7572.
Hz, J = 1.5 Hz, 4-H), 7.38 (dd, J = J7¢,8¢ = 8.1 Hz, 7¢-
4,2 7¢,6¢
4
12) Reviews: (a) Lohray, B. B. Tetrahedron: Asymmetry 1992,
H), 7.68 (dd, J8¢,7¢ = 8.4 Hz, J = 1.1 Hz, 8¢-H).
8¢,6¢
3
, 1317. (b) Johnson, R. A.; Sharpless, K. B. Asymmetric
(23) The enantioselectivities were determined by HPLC.
Column: Chiralcel OD-H No. ODHOCE-AJ071; Daicel
Chemical Ind. Ltd.; eluent: n-heptane–EtOH (60:40); flow
Catalysis in Organic Synthesis; Ojima, I., Ed.; VCH: New
York, 1993, 227. (c) Kolb, H. C.; VanNieuwenhze, M. S.;
Sharpless, K. B. Chem. Rev. 1994, 94, 2483. (d) Bolm, C.;
Hildebrand, J. P.; Muniz, K. In Catalytic Asymmetric
Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York,
rate; 0.6 mL/min; UV detector: 233 nm; t : 12.3 min for 10,
R
14.7 min for ent-10.
(24) (a) Pyrek, J. S.; Achmatowicz, O. Jr.; Zamojski, A.
Tetrahedron 1977, 33, 673. (b) DeNinno, M. P.;
2
000, 399.
13) (a) Harcken, C.; Brückner, R. Angew. Chem., Int. Ed. Engl.
997, 36, 2750; Angew. Chem. 1997, 109, 2866.
b) Harcken, C.; Brückner, R.; Rank, E. Chem.–Eur. J. 1998,
, 2342; corrigendum: Harcken, C.; Brückner, R.; Rank, E.
(
Schoenleber, R.; Perner, R. J.; Lijewski, L.; Asin, K. E.;
Britton, D. R.; MacKenzie, R.; Kebabian, J. W. J. Med.
Chem. 1991, 34, 2561. (c) DeNinno, M. P.; Perner, R. J.;
Morton, H. E.; DiDomenico, S. Jr. J. Org. Chem. 1992, 57,
7115. (d) Masquelin, T.; Hengartner, U.; Streith, J. Synthesis
1995, 780. (e) Masquelin, T.; Hengartner, U.; Streith, J.
Helv. Chim. Acta 1997, 80, 43. (f) Giles, G. F.; Rickards, R.
W.; Senanayake, B. S. J. Chem. Soc., Perkin Trans. 1 1998,
3949. (g) Contant, P.; Haess, M.; Riegl, J.; Scalone, M.;
Visnick, M. Synthesis 1999, 821. (h) Bianchi, D. A.; Rua,
F.; Kaufman, T. S. Tetrahedron Lett. 2004, 45, 411.
1
(
4
Chem.–Eur. J. 1998, 4, 2390. (c) Berkenbusch, T.;
Brückner, R. Tetrahedron 1998, 54, 11461.
(
d) Berkenbusch, T.; Brückner, R. Tetrahedron 1998, 54,
11471. (e) Harcken, C.; Brückner, R. New J. Chem. 2001,
25, 40. (f) Harcken, C.; Brückner, R. Synlett 2001, 718.
(
3
g) Harcken, C.; Brückner, R. Tetrahedron Lett. 2001, 42,
967. (h) Kapferer, T.; Brückner, R.; Herzig, A.; König, W.
A. Chem.–Eur. J. 2005, 11, 2154.
14) Method: (a) Using 8a: Ragoussis, N. Tetrahedron Lett.
(25) This was inferred from the high-field shifts of the italicized
1
(
(
resonances in our H NMR spectrum (500 MHz, CDCl ;
3
1
987, 28, 93. (b) Using 8a or 8b: Yamanaka, H.; Yokoyama,
d3a-H = 4.37, d5-H = 5.07, and d
the values published (ref. ) for the trans,cis-isomer:
d3a-H = 4.73, d5-H = 5.37, and d11b-H = 5.58 ppm. Ref.
reports a similar shift difference for the analogous signals of
cis,cis-20 (d values in analogous order: d = 4.27, 4.84, and
5.33 ppm) vs. trans,cis-20 (d values in analogous order:
d = 4.61, 4.96, and 5.33 ppm). See Figure 2.
= 5.59 ppm) relative to
11b-H
1
1b
M.; Sakamoto, T.; Shiraishi, T.; Sagi, M.; Mizugaki, M.
Heterocycles 1983, 20, 1541.
1
0f
15) (a) Arndt–Eistert homologation of a,b-unsaturated
carboxylic chlorides: Moore, J. A. J. Org. Chem. 1955, 20,
1607. (b) Syntheses of a,b-unsaturated diazoketones from
a,b-unsaturated carboxylic chlorides: Berenbom, M.; Fones,
W. S. J. Org. Chem. 1949, 14, 1629. (c) Ceccherelli, P.;
Synlett 2005, No. 8, 1281–1285 © Thieme Stuttgart · New York