-
1
-
-
33646481443
-
-
note
-
This course was given at the University of Michigan by the senior author's doctoral advisor, Prof. Masato Koreeda, to whom we are pleased to dedicate this article.
-
-
-
-
6
-
-
0043154087
-
-
Review:. Pearson W.H. (Ed), JAI, Greenwich, CT
-
Review:. Ciufolini M.A. In: Pearson W.H. (Ed). Advances in Heterocyclic Natural Product Synthesis, Vol. 3 (1996), JAI, Greenwich, CT 1
-
(1996)
Advances in Heterocyclic Natural Product Synthesis, Vol. 3
, pp. 1
-
-
Ciufolini, M.A.1
-
7
-
-
33646467308
-
-
See also:
-
-
-
-
9
-
-
33646467021
-
-
note
-
50≈510 nM; tests conducted at the U.S. NCI).
-
-
-
-
11
-
-
0033549831
-
-
Boger D.L., Lederboer M.W., Kume M., and Jin Q. Angew. Chem., Int. Ed. 38 (1999) 2424
-
(1999)
Angew. Chem., Int. Ed.
, vol.38
, pp. 2424
-
-
Boger, D.L.1
Lederboer, M.W.2
Kume, M.3
Jin, Q.4
-
12
-
-
0033572757
-
-
Boger D.L., Lederboer M.W., Kume M., Searcey M., and Jin Q. J. Am. Chem. Soc. 121 (1999) 11375
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(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 11375
-
-
Boger, D.L.1
Lederboer, M.W.2
Kume, M.3
Searcey, M.4
Jin, Q.5
-
15
-
-
33646487567
-
-
Review:
-
-
-
-
16
-
-
77957080395
-
-
Harmata M. (Ed), Elsevier, Amsterdam, The Netherlands
-
Ciufolini M.A. In: Harmata M. (Ed). Strategies and Tactics in Organic Synthesis, Vol. 6 (2005), Elsevier, Amsterdam, The Netherlands 1
-
(2005)
Strategies and Tactics in Organic Synthesis, Vol. 6
, pp. 1
-
-
Ciufolini, M.A.1
-
17
-
-
33646494130
-
-
Isolation:
-
-
-
-
18
-
-
0030048612
-
-
Sakamoto K., Tsujii E., Abe F., Nakanishi T., Yamashita M., Shigematsu N., Izumi S., and Okuhara M. J. Antibiot. 49 (1996) 37
-
(1996)
J. Antibiot.
, vol.49
, pp. 37
-
-
Sakamoto, K.1
Tsujii, E.2
Abe, F.3
Nakanishi, T.4
Yamashita, M.5
Shigematsu, N.6
Izumi, S.7
Okuhara, M.8
-
19
-
-
33646486047
-
-
Enantiocontrolled total syntheses:
-
-
-
-
22
-
-
33646477369
-
-
Syntheses of the racemate:
-
-
-
-
24
-
-
4344580504
-
-
Kan T., Fujimoto T., Ieda S., Asoh Y., Kitaoka H., and Fukuyama T. Org. Lett. 6 (2004) 2729
-
(2004)
Org. Lett.
, vol.6
, pp. 2729
-
-
Kan, T.1
Fujimoto, T.2
Ieda, S.3
Asoh, Y.4
Kitaoka, H.5
Fukuyama, T.6
-
25
-
-
33646472229
-
-
Synthetic studies:
-
-
-
-
29
-
-
33646477510
-
-
Kropf, J. E.; Weinreb, S. M. Abstracts of Papers, 222nd National Meeting of the American Chemical Society, Chicago, IL, Aug 26-30, 2001; American Chemical Society: Washington, DC, 2001; ORGN 373;
-
-
-
-
30
-
-
0033400773
-
-
Bonjoch J., Diaba F., Puigbo E., Sole D., Segarra V., Santamaria L., Beleta J., Ryder H., and Palacios J.-M. Bioorg. Med. Chem. 7 (1999) 2891
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(1999)
Bioorg. Med. Chem.
, vol.7
, pp. 2891
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Bonjoch, J.1
Diaba, F.2
Puigbo, E.3
Sole, D.4
Segarra, V.5
Santamaria, L.6
Beleta, J.7
Ryder, H.8
Palacios, J.-M.9
-
38
-
-
33646492413
-
-
Shirafuji, H.; Tsubotani, S.; Ishimaru, T.; Harada, S. (Takeda Chemical Industries, Ltd.) WO91/13887, 1991
-
-
-
-
39
-
-
33646476799
-
-
Implicit in the formulation of Scheme 4 is the notion that 21 will advance to spirolactam 20 through oxidative conversion of the phenol to an electrophilic species, perhaps a cationic agent of the type 27 (cf. Scheme 6), which is then captured by the nitrogen atom of the amide. The N atom thus expresses nucleophilic character in this transformation. Complementary reactions also leading to spirolactams, but involving reaction of an electron-rich aromatic ring with an electrophilic N atom, were known prior to our work. Notable in this regard is the chemistry of N-alkoxy-acylnitrenium species (cf.
-
-
-
-
40
-
-
0348241629
-
-
Glover S.A., Goosen A., McCleland C.W., and Schoonraad J.L. J. Chem. Soc., Perkin Trans. 1 (1984) 2255
-
(1984)
J. Chem. Soc., Perkin Trans. 1
, pp. 2255
-
-
Glover, S.A.1
Goosen, A.2
McCleland, C.W.3
Schoonraad, J.L.4
-
45
-
-
0001416368
-
-
), which in recent years has revealed its full synthetic potential thanks to the work of Wardrop
-
Kikugawa Y., Shimada M., and Matsumoto K. Heterocycles 37 (1994) 293 ), which in recent years has revealed its full synthetic potential thanks to the work of Wardrop
-
(1994)
Heterocycles
, vol.37
, pp. 293
-
-
Kikugawa, Y.1
Shimada, M.2
Matsumoto, K.3
-
46
-
-
33646492733
-
-
For leading references see:
-
-
-
-
50
-
-
0037450947
-
-
See also Refs. 9k, 21g and 35v.
-
Wardrop D.J., Burge M.S., Zhang W., and Ortiz J.A. Tetrahedron Lett. 44 (2003) 2587 See also Refs. 9k, 21g and 35v.
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(2003)
Tetrahedron Lett.
, vol.44
, pp. 2587
-
-
Wardrop, D.J.1
Burge, M.S.2
Zhang, W.3
Ortiz, J.A.4
-
52
-
-
33646467895
-
-
See also:
-
-
-
-
53
-
-
0000179169
-
-
Kita Y., Tohma H., Kikuchi K., Inagaki M., and Yakura T. J. Org. Chem. 56 (1991) 435
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(1991)
J. Org. Chem.
, vol.56
, pp. 435
-
-
Kita, Y.1
Tohma, H.2
Kikuchi, K.3
Inagaki, M.4
Yakura, T.5
-
54
-
-
0342458391
-
-
Pearson W.H. (Ed), JAI, Greenwich, CT
-
Knapp S. In: Pearson W.H. (Ed). Advances in Heterocyclic Natural Product Synthesis, Vol. 3 (1996), JAI, Greenwich, CT 57
-
(1996)
Advances in Heterocyclic Natural Product Synthesis, Vol. 3
, pp. 57
-
-
Knapp, S.1
-
55
-
-
0000316483
-
-
Oxazolines also participate effectively in iodolactamization reactions:
-
Oxazolines also participate effectively in iodolactamization reactions:. Kurth M.J., and Bloom S.H. J. Org. Chem. 54 (1989) 411
-
(1989)
J. Org. Chem.
, vol.54
, pp. 411
-
-
Kurth, M.J.1
Bloom, S.H.2
-
58
-
-
33646489260
-
-
For example the Wipf method: reference
-
-
-
-
63
-
-
0034647499
-
-
Braun N.A., Ousmer M., Bray J.D., Bouchu D., Peters K., Peters E.-M., and Ciufolini M.A. J. Org. Chem. 65 (2000) 4397
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(2000)
J. Org. Chem.
, vol.65
, pp. 4397
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-
Braun, N.A.1
Ousmer, M.2
Bray, J.D.3
Bouchu, D.4
Peters, K.5
Peters, E.-M.6
Ciufolini, M.A.7
-
64
-
-
0000892411
-
-
This entails conduct of the reaction in fluorinated alcohol solvents such as hexafluoro-2-propanol (HFIP) or trifluoroethanol (TFE). Cf. Ref. 12 as well as:
-
This entails conduct of the reaction in fluorinated alcohol solvents such as hexafluoro-2-propanol (HFIP) or trifluoroethanol (TFE). Cf. Ref. 12 as well as:. Kita Y., Takada T., Gyoten M., Tohma H., Zenk M.H., and Eichhorn J. J. Org. Chem. 61 (1996) 5857
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(1996)
J. Org. Chem.
, vol.61
, pp. 5857
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-
Kita, Y.1
Takada, T.2
Gyoten, M.3
Tohma, H.4
Zenk, M.H.5
Eichhorn, J.6
-
65
-
-
33646472697
-
-
Cf.:
-
-
-
-
67
-
-
0002571384
-
-
Lunazzi L., Cerioni G., Foresti E., and Macciantelli D. J. Chem. Soc., Perkin Trans. 2 (1980) 717
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(1980)
J. Chem. Soc., Perkin Trans. 2
, pp. 717
-
-
Lunazzi, L.1
Cerioni, G.2
Foresti, E.3
Macciantelli, D.4
-
68
-
-
33646485885
-
-
See also:
-
-
-
-
70
-
-
0037170642
-
-
For additional applications of this transformation, which one may rightfully describe as the Sorensen reaction, see, e.g.:
-
For additional applications of this transformation, which one may rightfully describe as the Sorensen reaction, see, e.g.:. Mizutani H., Takayama J., Soeda Y., and Honda T. Tetrahedron Lett. 43 (2002) 2411
-
(2002)
Tetrahedron Lett.
, vol.43
, pp. 2411
-
-
Mizutani, H.1
Takayama, J.2
Soeda, Y.3
Honda, T.4
-
71
-
-
33646485747
-
-
Synthesis of TAN1251 substances:
-
-
-
-
72
-
-
0032543489
-
-
Nagumo S., Nishida A., Yamazaki C., Murashige K., and Kawahara N. Tetrahedron Lett. 39 (1998) 4493
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 4493
-
-
Nagumo, S.1
Nishida, A.2
Yamazaki, C.3
Murashige, K.4
Kawahara, N.5
-
75
-
-
0037054215
-
-
Nagumo S., Nishida A., Yamazaki C., Matoba A., Murashige K., and Kawahara N. Tetrahedron 58 (2002) 4917
-
(2002)
Tetrahedron
, vol.58
, pp. 4917
-
-
Nagumo, S.1
Nishida, A.2
Yamazaki, C.3
Matoba, A.4
Murashige, K.5
Kawahara, N.6
-
76
-
-
0037010763
-
-
Nagumo S., Matoba A., Ishii Y., Yamaguchi S., Akutsu N., Nishijima H., Nishida A., and Kawahara N. Tetrahedron 58 (2002) 9871
-
(2002)
Tetrahedron
, vol.58
, pp. 9871
-
-
Nagumo, S.1
Matoba, A.2
Ishii, Y.3
Yamaguchi, S.4
Akutsu, N.5
Nishijima, H.6
Nishida, A.7
Kawahara, N.8
-
78
-
-
33646472377
-
-
Synthetic studies:
-
-
-
-
85
-
-
0034807908
-
-
Ousmer M., Braun N.A., Bavoux C., Perrin M., and Ciufolini M.A. J. Am. Chem. Soc. 123 (2001) 7543
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 7543
-
-
Ousmer, M.1
Braun, N.A.2
Bavoux, C.3
Perrin, M.4
Ciufolini, M.A.5
-
87
-
-
0034716554
-
-
Myers A.G., Zhong B., Movassaghi M., Kung D.W., Lanman B.A., and Kwon S. Tetrahedron Lett. 41 (2000) 1359
-
(2000)
Tetrahedron Lett.
, vol.41
, pp. 1359
-
-
Myers, A.G.1
Zhong, B.2
Movassaghi, M.3
Kung, D.W.4
Lanman, B.A.5
Kwon, S.6
-
89
-
-
0034687186
-
-
Myers A.G., Zhong B., Kung D.W., Movassaghi M., Lanman B.A., and Kwon S. Org. Lett. 2 (2000) 3337
-
(2000)
Org. Lett.
, vol.2
, pp. 3337
-
-
Myers, A.G.1
Zhong, B.2
Kung, D.W.3
Movassaghi, M.4
Lanman, B.A.5
Kwon, S.6
-
90
-
-
33646466742
-
-
For example:
-
-
-
-
94
-
-
17244375099
-
-
Charest M.G., Lerner C.D., Brubaker J.D., Siegel D.R., and Myers A.G. Science 308 (2005) 395
-
(2005)
Science
, vol.308
, pp. 395
-
-
Charest, M.G.1
Lerner, C.D.2
Brubaker, J.D.3
Siegel, D.R.4
Myers, A.G.5
-
97
-
-
33646489733
-
-
note
-
The lactam unit in 57 is much less C-H acidic than either the ketone or the aldehyde, and it was anticipated not to interfere with the operations leading to the tricyclic aldol intermediate.
-
-
-
-
99
-
-
33646491111
-
-
note
-
Dielectric constants at 25 °C (CRC Handbook of Chemistry and Physics, 59th Ed.): t-BuOH=10.9; EtOH=24.3; MeOH=32.6.
-
-
-
-
100
-
-
33646487100
-
-
note
-
The OH group is more accessible in the less sterically hindered MeOH and EtOH relative to the more sterically encumbered t-BuOH. This should result in stronger H-bonds.
-
-
-
-
102
-
-
33646483612
-
-
note
-
We are grateful to the Fujisawa Co. for a sample of nature FR-901483.
-
-
-
-
103
-
-
0027301895
-
-
Blackman A.J., Li C., Hockless D.C.R., Skelton B.W., and White A.H. Tetrahedron 49 (1993) 8645
-
(1993)
Tetrahedron
, vol.49
, pp. 8645
-
-
Blackman, A.J.1
Li, C.2
Hockless, D.C.R.3
Skelton, B.W.4
White, A.H.5
-
106
-
-
33646486967
-
-
note
-
The absolute configuration of natural cylindricines remains unknown. We focused on (-)-cylindricine C, 76, only because we intended to compare our ultimate product with that described by Molander (Ref. 35a), who at the onset of our investigations was the sole author to have achieved the enantiocontrolled synthesis of a cylindricine.
-
-
-
-
107
-
-
33646485061
-
-
Enantiocontrolled syntheses of various cylindricines:
-
-
-
-
109
-
-
33646474533
-
-
C, D, and E:
-
-
-
-
114
-
-
33646475074
-
-
Syntheses of (±)-cylindricines:
-
-
-
-
117
-
-
33646474948
-
-
(±)-4-Epicylindricine C:
-
-
-
-
119
-
-
33646493277
-
-
Synthetic studies:
-
-
-
-
122
-
-
18744402534
-
-
Taniguchi T., Tamura O., Uchiyama M., Muraoka O., Tanabe G., and Ishibashi H. Synlett (2005) 1179
-
(2005)
Synlett
, pp. 1179
-
-
Taniguchi, T.1
Tamura, O.2
Uchiyama, M.3
Muraoka, O.4
Tanabe, G.5
Ishibashi, H.6
-
124
-
-
33646483882
-
-
Studies on structurally related alkaloids:
-
-
-
-
136
-
-
33646494129
-
-
note
-
The unnatural aminoacid, homotyrosine, is commercially available in either enantiomeric form
-
-
-
-
137
-
-
0033536632
-
-
Zhou W.-S., Lu Z.-H., Xu Y.-M., Liao L.-X., and Wang Z.-M. Tetrahedron 55 (1999) 11959
-
(1999)
Tetrahedron
, vol.55
, pp. 11959
-
-
Zhou, W.-S.1
Lu, Z.-H.2
Xu, Y.-M.3
Liao, L.-X.4
Wang, Z.-M.5
-
138
-
-
0001381255
-
-
Review:
-
Review:. Ciufolini M.A., Hermann C.Y.W., Dong Q., Shimizu T., Swaminathan S., and Xi N. Synlett (1998) 105
-
(1998)
Synlett
, pp. 105
-
-
Ciufolini, M.A.1
Hermann, C.Y.W.2
Dong, Q.3
Shimizu, T.4
Swaminathan, S.5
Xi, N.6
-
139
-
-
0037100007
-
-
Canesi S., Belmont P., Bouchu D., Rousset L., and Ciufolini M.A. Tetrahedron Lett. 43 (2002) 5193
-
(2002)
Tetrahedron Lett.
, vol.43
, pp. 5193
-
-
Canesi, S.1
Belmont, P.2
Bouchu, D.3
Rousset, L.4
Ciufolini, M.A.5
-
141
-
-
33646491381
-
-
note
-
In principle, all cylindricines may be obtained by appropriate manipulations of cylindricine C, which therefore is a privileged target for chemical synthesis.
-
-
-
-
142
-
-
0042530467
-
-
Other protecting groups afforded inferior diastereoselectivities. For the use of bulky silyl groups to direct facial selectivity in a different context see, e.g.:
-
Other protecting groups afforded inferior diastereoselectivities. For the use of bulky silyl groups to direct facial selectivity in a different context see, e.g.:. Clive D.L.J., and Wang J. Angew. Chem., Int. Ed. 42 (2003) 3406
-
(2003)
Angew. Chem., Int. Ed.
, vol.42
, pp. 3406
-
-
Clive, D.L.J.1
Wang, J.2
-
144
-
-
33646489734
-
-
For a discussion see:
-
-
-
-
146
-
-
33646493278
-
-
See also
-
-
-
-
147
-
-
0034638792
-
-
and refs. cited therein
-
Bennabi S., Narkunan K., Rousset L., Bouchu D., and Ciufolini M.A. Tetrahedron Lett. 41 (2000) 8873, and refs. cited therein
-
(2000)
Tetrahedron Lett.
, vol.41
, pp. 8873
-
-
Bennabi, S.1
Narkunan, K.2
Rousset, L.3
Bouchu, D.4
Ciufolini, M.A.5
-
149
-
-
0035906463
-
-
Weaker bases were ineffective. This is in complete accord with:
-
Weaker bases were ineffective. This is in complete accord with:. Paquette L.A., Ra S.C., Schloss J.D., Leit S.M., and Gallucci J.C. J. Org. Chem. 66 (2001) 3564
-
(2001)
J. Org. Chem.
, vol.66
, pp. 3564
-
-
Paquette, L.A.1
Ra, S.C.2
Schloss, J.D.3
Leit, S.M.4
Gallucci, J.C.5
-
151
-
-
33646486499
-
-
See also:
-
-
-
-
155
-
-
33646493602
-
-
note
-
® (registered trademark of the DuPont Co.). Presumably, this Bronsted acidic reagent rapidly protonated the tertiary amino group in 107, thereby suppressing possible interference during oxidation of the thioether.
-
-
-
-
158
-
-
33646486344
-
-
For amine-directed organocuprate additions see, e.g.:
-
-
-
-
160
-
-
33646466741
-
-
Bibliography on directed organocuprate additions:
-
-
-
-
162
-
-
0025364262
-
-
Evans D.A., Clark J.S., Metternich R., Novack V.J., and Sheppard G.S. J. Am. Chem. Soc. 112 (1990) 866
-
(1990)
J. Am. Chem. Soc.
, vol.112
, pp. 866
-
-
Evans, D.A.1
Clark, J.S.2
Metternich, R.3
Novack, V.J.4
Sheppard, G.S.5
-
164
-
-
33646492732
-
-
note
-
By contrast, the Wardrop cyclization of N-alkoxy-acylnitrenium ions (Refs. 11g-j) leading to N-alkoxy piperidinones occurs efficiently.
-
-
-
-
165
-
-
33646476948
-
-
note
-
These experiments were inspired by the success of our sulfonamide-based methodology (Ref. 3).
-
-
-
-
166
-
-
33646485197
-
-
Leading references and noteworthy examples of reactions of this type: see Refs. 11 as well as:
-
-
-
-
171
-
-
0042509905
-
-
Kikugawa Y., Nagashima A., Sakamoto T., Miyazawa E., and Shiiya M. J. Org. Chem. 68 (2003) 6739
-
(2003)
J. Org. Chem.
, vol.68
, pp. 6739
-
-
Kikugawa, Y.1
Nagashima, A.2
Sakamoto, T.3
Miyazawa, E.4
Shiiya, M.5
-
173
-
-
0036008095
-
-
Prata J.V., Clemente D.-T.S., Prabhakar S., Lobo A.M., Mourato I., and Branco P.S. J. Chem. Soc., Perkin Trans. 1 (2002) 513
-
(2002)
J. Chem. Soc., Perkin Trans. 1
, pp. 513
-
-
Prata, J.V.1
Clemente, D.-T.S.2
Prabhakar, S.3
Lobo, A.M.4
Mourato, I.5
Branco, P.S.6
-
174
-
-
0028270363
-
-
Telma D., Clemente V., Lobo A.M., Prabhakar S., and Marcelo-Curto M.J. Tetrahedron Lett. 35 (1994) 2043
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 2043
-
-
Telma, D.1
Clemente, V.2
Lobo, A.M.3
Prabhakar, S.4
Marcelo-Curto, M.J.5
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