-
6
-
-
0000207195
-
-
S.A. Achmad, T. Høyer, A. Kjær, L. Makmur, and R. Norrestam Acta Chem. Scand. 41B 1987 599 609
-
(1987)
Acta Chem. Scand.
, vol.41
, pp. 599-609
-
-
Achmad, S.A.1
Høyer, T.2
Kjær, A.3
Makmur, L.4
Norrestam, R.5
-
8
-
-
0001195233
-
-
A. Alemany, C. Márquez, C. Pascual, S. Valverde, M. Martínez-Ripoll, J. Fayos, and A. Perales Tetrahedron Lett. 20 1979 3583 3586
-
(1979)
Tetrahedron Lett.
, vol.20
, pp. 3583-3586
-
-
Alemany, A.1
Márquez, C.2
Pascual, C.3
Valverde, S.4
Martínez- Ripoll, M.5
Fayos, J.6
Perales, A.7
-
11
-
-
0021017333
-
-
For studies on the biological properties of lactones containing a 6-substituted 5,6-dihydropyran-2-one moiety, see, for example: (a) S.S. Stampwala, R.H. Bunge, T.R. Hurley, N.E. Willmer, A.J. Brankiewicz, C.E. Steinman, T.A. Smitka, and J.C. French J. Antibiot. 36 1983 1601 1605
-
(1983)
J. Antibiot.
, vol.36
, pp. 1601-1605
-
-
Stampwala, S.S.1
Bunge, R.H.2
Hurley, T.R.3
Willmer, N.E.4
Brankiewicz, A.J.5
Steinman, C.E.6
Smitka, T.A.7
French, J.C.8
-
14
-
-
0035218054
-
-
G.E. Raoelison, C. Terreaux, E.F. Queiroz, F. Zsila, M. Simonyi, S. Antus, A. Randriantsoa, and K. Hostettmann Helv. Chim. Acta 84 2001 3470 3476
-
(2001)
Helv. Chim. Acta
, vol.84
, pp. 3470-3476
-
-
Raoelison, G.E.1
Terreaux, C.2
Queiroz, E.F.3
Zsila, F.4
Simonyi, M.5
Antus, S.6
Randriantsoa, A.7
Hostettmann, K.8
-
19
-
-
0027245973
-
-
R. Pereda-Miranda, L. Hernández, M.J. Villavicencio, M. Novelo, P. Ibarra, H. Chai, and J.M. Pezzuto J. Nat. Prod. 56 1993 583 593
-
(1993)
J. Nat. Prod.
, vol.56
, pp. 583-593
-
-
Pereda-Miranda, R.1
Hernández, L.2
Villavicencio, M.J.3
Novelo, M.4
Ibarra, P.5
Chai, H.6
Pezzuto, J.M.7
-
22
-
-
0000591350
-
-
S. Valverde, A. Hernández, B. Herradón, R.M. Rabanal, and M. Martín-Lomas Tetrahedron 43 1987 3499 3504
-
(1987)
Tetrahedron
, vol.43
, pp. 3499-3504
-
-
Valverde, S.1
Hernández, A.2
Herradón, B.3
Rabanal, R.M.4
Martín-Lomas, M.5
-
23
-
-
0037463510
-
-
(a) For a preliminary account of the synthesis of 1, see: J. Murga, J. García-Fortanet, M. Carda, and J.A. Marco Tetrahedron Lett. 44 2003 1737 1739
-
(2003)
Tetrahedron Lett.
, vol.44
, pp. 1737-1739
-
-
Murga, J.1
García-Fortanet, J.2
Carda, M.3
Marco, J.A.4
-
24
-
-
0037662050
-
-
(b) For a full description of the synthesis of 2 and several analoga, including a study of their cytotoxic properties, see: E. Falomir, J. Murga, P. Ruiz, M. Carda, J.A. Marco, R. Pereda-Miranda, M. Fragoso-Serrano, and C.M. Cerda-García-Rojas J. Org. Chem. 68 2003 5672 5676
-
(2003)
J. Org. Chem.
, vol.68
, pp. 5672-5676
-
-
Falomir, E.1
Murga, J.2
Ruiz, P.3
Carda, M.4
Marco, J.A.5
Pereda-Miranda, R.6
Fragoso-Serrano, M.7
Cerda-García-Rojas, C.M.8
-
25
-
-
1542298882
-
-
(c) For a full description of the synthesis of 3, see: S. Díaz-Oltra, J. Murga, E. Falomir, M. Carda, and J.A. Marco Tetrahedron 60 2004 2979 2985
-
(2004)
Tetrahedron
, vol.60
, pp. 2979-2985
-
-
Díaz-Oltra, S.1
Murga, J.2
Falomir, E.3
Carda, M.4
Marco, J.A.5
-
26
-
-
0037031711
-
-
For other syntheses of our group, where the same concept was used, see: (a) M. Carda, S. Rodríguez, B. Segovia, and J.A. Marco J. Org. Chem. 67 2002 6560 6563
-
(2002)
J. Org. Chem.
, vol.67
, pp. 6560-6563
-
-
Carda, M.1
Rodríguez, S.2
Segovia, B.3
Marco, J.A.4
-
27
-
-
0037415524
-
-
M. Carda, S. Rodríguez, E. Castillo, A. Bellido, S. Díaz-Oltra, and J.A. Marco Tetrahedron 59 2003 857 864
-
(2003)
Tetrahedron
, vol.59
, pp. 857-864
-
-
Carda, M.1
Rodríguez, S.2
Castillo, E.3
Bellido, A.4
Díaz-Oltra, S.5
Marco, J.A.6
-
33
-
-
0037000811
-
-
For a recent review on asymmetric allylborations, see: P.V. Ramachandran Aldrichimica Acta 35 2002 23 35
-
(2002)
Aldrichimica Acta
, vol.35
, pp. 23-35
-
-
Ramachandran, P.V.1
-
35
-
-
9644305469
-
-
note
-
The use of two different silyl groups (e.g. TES and TBS) is not necessary in principle. However, we had initially planned the use of standard achiral ethynylating reagents (such as ethynylmagnesium bromide) in the reaction with 9. In anticipation of unsatisfactory diastereoselectivities in these reactions (as it turned out to be the case), we envisaged the oxidation of the resulting alcohols (10 +epimer) to a conjugated ynone, followed by stereoselective reduction. Since a free β-hydroxy carbonyl group might be convenient for that purpose, we placed an easily cleavable silyl group (TES) at this position. However, when we finally resorted to the asymmetric ethynylation of 9, we decided to maintain the already present TES group.
-
-
-
-
36
-
-
9644298564
-
-
note
-
2S, the asymmetric ethynylation to 11 did not work.
-
-
-
-
38
-
-
0041780219
-
-
In addition to trimethylsilylacetylene, we also used 2-methyl-3-butyn-2- ol: D. Boyall, F. López, H. Sasaki, D. Frantz, and E.M. Carreira Org. Lett. 2 2000 4233 4236 However, whereas the addition step was successful, all attempts to cleave the acetone fragment solely led to decomposition
-
(2000)
Org. Lett.
, vol.2
, pp. 4233-4236
-
-
Boyall, D.1
López, F.2
Sasaki, H.3
Frantz, D.4
Carreira, E.M.5
-
39
-
-
0035969627
-
-
Aside from the contributions of Carreira's group, we have found only few examples of the use of their asymmetric ethynylation methodology: (a) R.K. Dieter, and H. Yu Org. Lett. 3 2001 3855 3858
-
(2001)
Org. Lett.
, vol.3
, pp. 3855-3858
-
-
Dieter, R.K.1
Yu, H.2
-
40
-
-
0001320812
-
-
N. Maezaki, N. Kojima, M. Asai, H. Tominaga, and T. Tanaka Org. Lett. 4 2002 2977 2980
-
(2002)
Org. Lett.
, vol.4
, pp. 2977-2980
-
-
Maezaki, N.1
Kojima, N.2
Asai, M.3
Tominaga, H.4
Tanaka, T.5
-
42
-
-
0036349309
-
-
For a failure, see: (d) B.W. Gung, H.D. Dickson, S. Seggerson, and K. Bluhm Synth. Commun. 32 2002 2733 2740
-
(2002)
Synth. Commun.
, vol.32
, pp. 2733-2740
-
-
Gung, B.W.1
Dickson, H.D.2
Seggerson, S.3
Bluhm, K.4
-
43
-
-
0035968398
-
-
Further related enantioselective ethynylation methodologies have been recently reported. See, for example: (a) G. Lu, X.S. Li, Z.Y. Zhou, W.L. Chan, and A.S.C. Chan Tetrahedron: Asymmetry 12 2001 2147 2152
-
(2001)
Tetrahedron: Asymmetry
, vol.12
, pp. 2147-2152
-
-
Lu, G.1
Li, X.S.2
Zhou, Z.Y.3
Chan, W.L.4
Chan, A.S.C.5
|