2642 J ournal of Medicinal Chemistry, 2002, Vol. 45, No. 12
Lampe et al.
ent-Staurosporine. J . Am. Chem. Soc. 1995, 117, 552-553 and
references therein. (b) Garcia-Echeverria, C.; Traxler, P.; Evans,
D. B. ATP Site-Directed Competitive and Irreversible Inhibitors
of Protein Kinases. Med. Res. Rev. 2000, 20, 28-57.
(15) (a) Heerding, J . M.; Lampe, J . W.; Darges, J . W.; Stamper, M.
L. Protein Kinase C Inhibitory Activities of Balanol Analogs
Bearing Carboxylic Acid Replacements. Bioorg. Med. Chem. Lett.
1995, 5, 1839-1842. (b) J agdmann, G. E., J r.; Defauw, J . M.;
Lai, Y.-S.; Crane, H. M.; Hall, S. E.; Buben, J . A.; Hu, H.; Gosnell,
P. A. Novel PKC Inhibitory Analogs of Balanol with Replacement
of the Ester Functionality. Bioorg. Med. Chem. Lett. 1995, 5,
2015-2020. (c) Crane, H. M.; Menaldino, D. S.; J agdmann, G.
E., J r.; Darges, J . W.; Buben, J . A. Increasing the Cellular PKC
Inhibitory Activity of Balanol: A Study of Ester Analogs. Bioorg.
Med. Chem. Lett. 1995, 5, 2133-2138. (d) Lai, Y.-S.; Stamper,
M. Heteroatom Effect in the PKC Inhibitory Activities of
Perhydroazepine Analogs of Balanol. Bioorg. Med. Chem. Lett.
1995, 5, 2147-2150. (e) Lai, Y.-S.; Menaldino, D. S.; Nichols, J .
B.; J agdmann, G. E., J r.; Mylott, F.; Gillespie, J .; Hall, S. E.
Ring Size Effect in the PKC Inhibitory Activities of Perhy-
droazepine Analogs of Balanol. Bioorg. Med. Chem. Lett. 1995,
5, 2151-2154. (f) Lai, Y.-S.; Mendoza, J . S.; Hubbard, F.; Kalter,
K. Synthesis and PKC Inhibitory Activities of Balanol Analogs
with a Cyclopentane Substructure. Bioorg. Med. Chem. Lett.
1995, 5, 2155-2160. (g) Mendoza, J . S.; J agdmann, G. E., J r.;
Gosnell, P. A. Synthesis and Biological Evaluation of Confor-
mationally Constrained Bicyclic and Tricyclic Balanol Analogues
as Inhibitors of Protein Kinase C. Bioorg. Med. Chem. Lett. 1995,
5, 2211-2216. (h) Defauw, J . M.; Murphy, M. M.; J agdmann,
G. E., J r.; Hu, H.; Lampe, J . W.; Hollinshead, S. P.; Mitchell, T.
J .; Crane, H. M.; Heerding, J . M.; Mendoza, J . S.; Davis, J . E.;
Darges, J . W.; Hubbard, F. R., Hall, S. E. Synthesis and Protein
Kinase C Inhibitory Activities of Acyclic Balanol Analogs that
are Highly Selectife for Protein Kinase C over Protein Kinase
A. J . Med. Chem. 1996, 39, 5215-5227. (i) J agdmann, G. E.,
J r.; Defauw, J . D.; Lampe, J . W.; Darges, J . W.; Kalter, K. Potent
and Selective PKC Inhibitory 5-membered Ring Analogs of
Balanol with Replacement of the Carboxamide Moiety. Bioorg.
Med. Chem. Lett. 1996, 6, 1759-1764. (j) Lai, Y.-S.; Mendoza,
J . S.; J agdmann, G. E., J r.; Menaldino, D. S.; Biggers, C. K.;
Heerding, J . M.; Wilson, J . W.; Hall, S. E., J iang, J . B.; J anzen,
W. P.; Ballas, L. M. Synthesis and Protein Kinase C. Inhibitory
Activities of Balanol Analogs with Replacement of the Perhy-
droazepine Moiety. J . Med. Chem. 1997, 40, 226-235.
(16) Koide, K.; Bunnage, M. E.; Paloma, L. G.; Kanter, J . R.; Taylor,
S. S.; Brunton, L. L.; Nicolaou, K. C. Molecular Design and
Biological Activity of Potent and Selective Protein Kinase
Inhibitors Related to Balanol. Chem. Biol. 1995, 2, 601-608.
(17) Horne, S.; Rodrigo, R. Anionic Fries rearrangement of esters of
ortho-iodobenzyl alcohols: rapid routes to estrone methyl ethyl
and its 9â-epimer and aryl naphthalide lignans. J . Chem. Soc.,
Chem. Commun. 1992, 164-166.
(18) J ohnson, M. G.; Foglesong, R. F. The Preparation of Hindered
Biphenyls Via the Suzuki Reaction. Tetrahedron Lett. 1997, 38,
7001-7002.
(19) (a) Hoshino, Y.; Miyaura, N.; Suzuki, A. Novel synthesis of
isoflavones by the palladium-catalyzed cross-coupling reaction
of 3-bromochromones with arylboronic acids or their esters. Bull.
Chem. Soc. J pn. 1988, 61, 3008-3010. (b) Satoh, M.; Miyaura,
N.; Suzuki, A. Cross-coupling reaction of alkyl- or arylboronic
acid esters with organic halides induced by thallium(I) salts and
palladium catalyst. Chem. Lett. 1989, 1405-1408.
(8) (a) Lampe, J . W.; Hughes, P. F.; Biggers, C. K.; Smith, S. H.;
Hu, H. Total Synthesis of (-)-Balanol. J . Org. Chem. 1994, 59,
5147-5148. (b) Hughes, P. F.; Smith, S. H.; Olson, J . T. Two
Chiral Syntheses of threo-3-Hydroxylysine. J . Org. Chem. 1994,
59, 5799-5802. (c) Hollinshead, S. E.; Nichols, J . B.; Wilson, J .
W. Two Practical Syntheses of Sterically Congested Benzophe-
nones. J . Org. Chem. 1994, 59, 6703-6709. (d) Hu, H.; J agd-
mann, G. E., J r.; Hughes, P. F.; Nichols, J . B. Two Efficient
Syntheses of (()-anti-N-Benzyl-3-amino-4-hydroxyhexahy-
droazepine. Tetrahedron Lett. 1995, 36, 3659-3662. (e) Lampe,
J . W.; Hughes, P. F.; Biggers, C. K.; Smith, S. H.; Hu, H. Total
Synthesis of (-)- and (+)-Balanol. J . Org. Chem. 1996, 61, 4572-
4581.
(9) (a) Nicolaou, K. C.; Bunnage, M. E.; Koide, K. Total Synthesis
of Balanol. J . Am. Chem. Soc. 1994, 116, 8402-8403. (b)
Nicolaou, K. C.; Koide, K.; Bunnage, M. E. Total Synthesis of
Balanol and Designed Analogues. Chem.sEur. J . 1995, 1, 454-
466.
(10) Adams, C. P.; Fairway, S. M.; Hardy, C. J .; Hibbs, D. E.;
Hursthouse, M. B.; Morley, A. D.; Sharp, B. W.; Vicker, N.;
Warner, I. Total Synthesis of Balanol: a Potent protein Kinase
C Inhibitor of Fungal Origin. J . Chem. Soc., Perkin Trans. 1
1995, 2355-2362.
(11) (a) Tanner, D.; Almario, A.; Hoegberg, T. Total synthesis of
balanol. Part 1. Enantioselective synthesis of the hexahy-
droazepine ring via chiral epoxides and aziridines. Tetrahedron
1995, 51, 6061-6070. (b) Tanner, D.; Tedenborg, L.; Almario,
A.; Pettersson, I.; Csoeregh, I.; Kelly, N. M.; Andersson, P. G.;
Hoegberg, T. Total synthesis of balanol. Part 2. Completion of
the synthesis and investigation of the structure and reactivity
of two key heterocyclic intermediates. Tetrahedron 1997, 53,
4857-4868.
(12) (a) Miyabe, H.; Torieda, M.; Kiguchi, T.; Naito, T. Total synthesis
of (-)-balanol. Synlett 1997, 580-582. (b) Miyabe, H.; Torieda,
M.; Inoue, K.; Tajiri, K.; Kiguchi, T.; Naito, T. Total Synthesis
of (-)-Balanol. J . Org. Chem. 1998, 63, 4397-4407.
(13) Formal total syntheses which focus on the benzophenone
subunit: (a) Denieul, M.-P.; Laursen, B.; Hazell, R.; Skrydstrup,
T. Synthesis of the Benzophenone Fragment of Balanol via an
Intramolecular Cyclization Event. J . Org. Chem. 2000, 65,
6052-6060. (b) Storm, J . P.; Andersson, C.-M. Iron-Mediated
Synthetic Routes to Unsymmetrically Substituted, Sterically
Congested Benzophenones. J . Org. Chem. 2000, 65, 5264-5274.
(14) Formal total syntheses which focus on the azepane subunit: (a)
Phansavath, P.; De Paule, S. D.; Ratovelomanana-Vidal, V.;
Genet, J .-P. An efficient formal synthesis of (-)-balanol by using
ruthenium-catalyzed asymmetric hydrogenation. Eur. J . Org.
Chem. 2000, 3903-3907. (b) Riber, D.; Hazell, R.; Skrydstrup,
T. Studies on the SmI2-Promoted Pinacol-Type Cyclization:
Synthesis of the Hexahydroazepine Ring of Balanol. J . Org.
Chem. 2000, 65, 5382-5390. (c) Masse, C. E.; Morgan, A. J .;
Panek, J . S. An Asymmetric Aminohydroxylation Approach to
the Azepine Core of (-)-Balanol. Org. Lett. 2000, 2, 2571-2573.
(d) Fuerstner, A.; Thiel, O. R. Formal Total Synthesis of (-)-
Balanol: Concise Approach to the Hexahydroazepine Segment
Based on RCM. J . Org. Chem. 2000, 65, 1738-1742. (e) Herdeis,
C.; Mohareb, R. M.; Neder, R. B.; Schwabenlander, F.; Telser,
J . Studies on the synthesis of chiral nonracemic 3,4-disubstituted
azepanes, a formal synthesis of (+)- and (-)-balanol. Tetrahe-
dron: Asymmetry 1999, 10, 4521-4537. (f) Cook, G. R.; Shanker,
P. S.; Peterson, S. L. Asymmetric Synthesis of the Balanol
Heterocycle via a Palladium-Mediated Epimerization and Olefin
Metathesis. Org. Lett. 1999, 1, 615-617. (g) Morie, T.; Kato, S.
New approach to (3R,4R)-3-amino-N′ benzyloxycarbonyl-4-hy-
droxyhexahydro-1H-azepine using ring expansion of optically
active piperidine derivative. Heterocycles 1998, 48, 427-431. (h)
Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.;
Zanirato, V. A unified asymmetric approach to substituted
hexahydroazepine and 7-azabicyclo[2.2.1]heptane ring systems
from D(-)-quinic acid: application to the formal syntheses of
(-)-balanol and (-)-epibatidine. Tetrahedron 1997, 53, 17177-
17194. (i) Wu, M. H.; J acobesen, E. N. An efficient formal
synthesis of balanol via the asymmetric epoxide ring opening
reaction. Tetrahedron Lett. 1997, 38, 1693-1696. (j) Tuch, A.;
Saniere, M.; Le Merrer, Y.; Depezay, J .-C. Synthesis of (2S,3R)-
3-amino-2-hydroxydecanoic acid and (3R,4R)-3-amino-4-hy-
droxyazepane from D-isoascorbic acid. Tetrahedron: Asymmetry
1996, 7, 2901-2909. (k) Naito, T.; Torieda, M.; Tajiri, K.;
Ninomiya, I.; Kiguchi, T. A novel and chiral synthesis of both
enantiomers of trans-3-amino-4-hydroxyhexahydroazepine, a key
intermediate for the synthesis of balanol. Chem. Pharm. Bull.
1996, 44, 624-626.
(20) Capson, T. L.; Poulter, C. D. A facile synthesis of primary amines
from carboxylic acids by the Curtius rearrangement. Tetrahe-
dron Lett. 1984, 25, 3515-3518.
(21) (a) Duncia, J . V.; Pierce, M. E.; Santella, J . B., III. Three
synthetic routes to a sterically hindered tetrazole. A new one-
step mild conversion of an amide into a tetrazole. J . Org. Chem.
1991, 56, 2395-2400. (b) Wittenberger, S. J .; Donner, B. G.
Dialkyltin oxide mediated addition of trimethylsilyl azide to
nitriles. A novel preparation of 5-substituted tetrazols. J . Org.
Chem. 1993, 58, 4139-4141.
(22) West, C. T.; Donnelly, S. J .; Kooistra, D. A.; Doyle, M. P. Silane
reductions in acidic media. II. Reductions of aryl aldehydes and
ketones by trialkylsilanes in trifluoroacetic acid. Selective
method for converting the carbonyl group to methylene. J . Org.
Chem. 1973, 38, 2675-2681.
(23) (a) Kulanthaivel, P.; J anzen, W. P.; Ballas, L. M.; J iang, J .; Hu,
C.-Q.; Darges, J . W.; Seldin, J .; Cofield, D.; Adams, L. Naturally
occurring protein kinase C inhibitors; II. Isolation of oligomeric
stilbenes from Caragana sinica. Planta Med. 1995, 61, 41-44.
(b) Kashiwada, Y.; Huang, L.; Ballas, L. M.; J iang, J . B.; J anzen,
W. P.; Lee, K.-H. New hexahydroxybiphenyl derivatives as
inhibitors of protein kinase C. J . Med. Chem. 1994, 37, 195-
200.
(24) Kashiwada, Y.; Nonaka, G.; Nishioka, I.; Ballas, L. M.; J iang,
J . B.; J anzen, W. P.; Lee, K.-H. Tannins as selective inhibitors
of protein kinase C. Bioorg. Med. Chem. Lett. 1992, 2, 239-244.
(25) (a) Erhardt, P. W.; Hagedorn, A. A., III; Sabio, M. Cardiotonic
Agents. 3. A Topographical Model of the Cardiac cAMP Phos-
phodiesterase Receptor. Mol. Pharmacol. 1988, 33, 1-13. (b)