-
1
-
-
56949106381
-
-
See, e.g.:
-
See, e.g.:
-
-
-
-
6
-
-
56949103530
-
-
For a few existing examples of elaborating 1 into apparent chiral building blocks, see:
-
For a few existing examples of elaborating 1 into apparent chiral building blocks, see:
-
-
-
-
10
-
-
56949086314
-
-
Compound 2 was first reported by White (obtained by a completely different approach):
-
Compound 2 was first reported by White (obtained by a completely different approach):
-
-
-
-
12
-
-
0001571279
-
-
White J.D., Badger R.A., Kezer H.S., Pallenberg A.J., and Schiehser G.A. Tetrahedron 45 (1989) 6631-6644
-
(1989)
Tetrahedron
, vol.45
, pp. 6631-6644
-
-
White, J.D.1
Badger, R.A.2
Kezer, H.S.3
Pallenberg, A.J.4
Schiehser, G.A.5
-
13
-
-
0033043159
-
-
The synthesis consisted of acetylation of all the hydroxyl groups, elimination of the acetoxyl group β to the carbonyl group, catalytic hydrogenation of the C-C double bond formed by the elimination, cleavage of the remaining acetyl groups, and selective formation of the terminal acetonide
-
Pedersen C. Carbohydr. Res. 315 (1999) 192-197 The synthesis consisted of acetylation of all the hydroxyl groups, elimination of the acetoxyl group β to the carbonyl group, catalytic hydrogenation of the C-C double bond formed by the elimination, cleavage of the remaining acetyl groups, and selective formation of the terminal acetonide
-
(1999)
Carbohydr. Res.
, vol.315
, pp. 192-197
-
-
Pedersen, C.1
-
14
-
-
0037969449
-
-
For the only synthesis involving 2 (not related to the routes of Refs. 3 and 4) so far documented, see:
-
For the only synthesis involving 2 (not related to the routes of Refs. 3 and 4) so far documented, see:. Watterson M.P., Edwards A.A., Leach J.A., Smith M.D., Ichihara O., and Fleet G.W.J. Tetrahedron Lett. 44 (2003) 5853-5857
-
(2003)
Tetrahedron Lett.
, vol.44
, pp. 5853-5857
-
-
Watterson, M.P.1
Edwards, A.A.2
Leach, J.A.3
Smith, M.D.4
Ichihara, O.5
Fleet, G.W.J.6
-
15
-
-
84988087864
-
-
Both 5 and 8 were previously synthesized from d-mannitol in 13.4% (6 steps) and 8.8% (7 steps), respectively. Chromatographic purification was required at each step therein. See:
-
Both 5 and 8 were previously synthesized from d-mannitol in 13.4% (6 steps) and 8.8% (7 steps), respectively. Chromatographic purification was required at each step therein. See:. Mulzer J., Pietschman C., Schöllhorn B., Buschmann J., and Luger P. Liebigs Ann. Chem. (1995) 1433-1439
-
(1995)
Liebigs Ann. Chem.
, pp. 1433-1439
-
-
Mulzer, J.1
Pietschman, C.2
Schöllhorn, B.3
Buschmann, J.4
Luger, P.5
-
16
-
-
56949092380
-
-
note
-
The hydrogenation was performed at 1 atm for 48 h (cf. 50 atm/12 h in Ref. 4).
-
-
-
-
17
-
-
0000941585
-
-
Martinelli M.J., Nayyar N.K., Moher E.D., Dhokte U.P., Pawlak J.M., and Vaidyanathan R. Org. Lett. 1 (1999) 447-450
-
(1999)
Org. Lett.
, vol.1
, pp. 447-450
-
-
Martinelli, M.J.1
Nayyar, N.K.2
Moher, E.D.3
Dhokte, U.P.4
Pawlak, J.M.5
Vaidyanathan, R.6
-
18
-
-
0037051615
-
-
Martinelli M.J., Vaidyanathan R., Pawlak J.M., Nayyar N.K., Dhokte U.P., Doecke C.W., Zollars L.M.H., Moher E.D., Van Khau V., and Kosmrlj B. J. Am. Chem. Soc. 124 (2002) 3578-3585
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 3578-3585
-
-
Martinelli, M.J.1
Vaidyanathan, R.2
Pawlak, J.M.3
Nayyar, N.K.4
Dhokte, U.P.5
Doecke, C.W.6
Zollars, L.M.H.7
Moher, E.D.8
Van Khau, V.9
Kosmrlj, B.10
-
19
-
-
56949101980
-
-
note
-
In the original method the water generated by formation of the intermediate cyclic stannylene acetals was distilled off azetropically (toluene). In this work, the water was removed by addition of activated 4 Å molecular sieves at ambient temperature.
-
-
-
-
20
-
-
0027771054
-
-
see, e.g.: where J=12.0 and 16.0 Hz were reported for the cis (16Za therein) and trans (16Ea therein) isomers, respectively, of a compound with an alkenyl structure very similar to that of 10
-
see, e.g.:. Leemhuis F.M.C., Thijs L., and Zwanenburg B. J. Org. Chem. 58 (1993) 7170-7179 where J=12.0 and 16.0 Hz were reported for the cis (16Za therein) and trans (16Ea therein) isomers, respectively, of a compound with an alkenyl structure very similar to that of 10
-
(1993)
J. Org. Chem.
, vol.58
, pp. 7170-7179
-
-
Leemhuis, F.M.C.1
Thijs, L.2
Zwanenburg, B.3
-
21
-
-
0001624567
-
-
Romeyke Y., Keller M., Kluge H., Grabley S., and Hammann P. Tetrahedron 47 (1991) 3335-3346
-
(1991)
Tetrahedron
, vol.47
, pp. 3335-3346
-
-
Romeyke, Y.1
Keller, M.2
Kluge, H.3
Grabley, S.4
Hammann, P.5
-
22
-
-
0034874829
-
-
(isolation)
-
Magiatis P., Spanakis D., Mitaku S., Tsitsa E., Mentis A., and Harvala C. J. Nat. Prod. 64 (2001) 1093-1094 (isolation)
-
(2001)
J. Nat. Prod.
, vol.64
, pp. 1093-1094
-
-
Magiatis, P.1
Spanakis, D.2
Mitaku, S.3
Tsitsa, E.4
Mentis, A.5
Harvala, C.6
-
29
-
-
9444224983
-
-
For literature precedents of cis (J=11.1 Hz) and trans (J=15.5 Hz) isomers of compounds with alkenyl structures very similar to that in 21 see: (the 5a and 5e therein, respectively)
-
For literature precedents of cis (J=11.1 Hz) and trans (J=15.5 Hz) isomers of compounds with alkenyl structures very similar to that in 21 see:. Ren H., Krasovskiy A., and Knochel P. Org. Lett. 6 (2004) 4215-4217 (the 5a and 5e therein, respectively)
-
(2004)
Org. Lett.
, vol.6
, pp. 4215-4217
-
-
Ren, H.1
Krasovskiy, A.2
Knochel, P.3
-
33
-
-
56949092782
-
-
note
-
Use of large excess of p-TsOH may lead to cleavage of the TBS protecting group.
-
-
-
-
34
-
-
0001616071
-
-
Yamaguchi M., Innaga J., Hirata K., Saeki H., and Katsuki T. Bull. Chem. Soc. Jpn. 52 (1979) 1989-1993
-
(1979)
Bull. Chem. Soc. Jpn.
, vol.52
, pp. 1989-1993
-
-
Yamaguchi, M.1
Innaga, J.2
Hirata, K.3
Saeki, H.4
Katsuki, T.5
-
35
-
-
4644323241
-
-
Fujioka H., Sawama Y., Murata N., Okitsu T., Kubo O., Matsuda S., and Kita Y. J. Am. Chem. Soc. 126 (2004) 11800-11801
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 11800-11801
-
-
Fujioka, H.1
Sawama, Y.2
Murata, N.3
Okitsu, T.4
Kubo, O.5
Matsuda, S.6
Kita, Y.7
-
41
-
-
33745685989
-
-
Iida A., Okazaki H., Misaki T., Sunagawa M., Sasaki A., and Tanabe Y. J. Org. Chem. 71 (2006) 5380-5383
-
(2006)
J. Org. Chem.
, vol.71
, pp. 5380-5383
-
-
Iida, A.1
Okazaki, H.2
Misaki, T.3
Sunagawa, M.4
Sasaki, A.5
Tanabe, Y.6
-
42
-
-
0001409192
-
-
Scheidt K.A., Chen H., Follows B.C., Chemler S.R., Coffey D.S., and Roush W.R. J. Org. Chem. 63 (1998) 6436-6437
-
(1998)
J. Org. Chem.
, vol.63
, pp. 6436-6437
-
-
Scheidt, K.A.1
Chen, H.2
Follows, B.C.3
Chemler, S.R.4
Coffey, D.S.5
Roush, W.R.6
-
43
-
-
0001527822
-
-
For instance, they may serve as precursors for the 1,3-diol fragments broadly found in natural products; the oxo polyene macrolide family antibiotics alone already contain more than 200 members. See:
-
For instance, they may serve as precursors for the 1,3-diol fragments broadly found in natural products; the oxo polyene macrolide family antibiotics alone already contain more than 200 members. See:. Rychnovsky S.D. Chem. Rev. 95 (1995) 2021-2040
-
(1995)
Chem. Rev.
, vol.95
, pp. 2021-2040
-
-
Rychnovsky, S.D.1
|