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Volumn 58, Issue 45, 2002, Pages 9209-9212

A novel synthetic method for (R)- and (S)-muscones by enantioselective hydrogenation of (E)- and (Z)-3-methyl-2-cyclopentadecen-1-ones catalyzed by p-tolyl-BINAP-Ru(II) complexes

(3) Yamamoto, Takeshi a Ogura, Miharu a Kanisawa, Tsuneyoshi a

a TAKASAGO INTERNATIONAL CORPORATION (Japan)

Author keywords

(E) and (Z) 3 methyl 2 cyclopentadecen 1 one; (R) and (S) muscone; Asymmetric hydrogenation; p tolyl BINAP Ru(II)

Indexed keywords

KETONE DERIVATIVE; MUSCONE; RUTHENIUM COMPLEX;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CATALYST; ENANTIOMER; ENANTIOSELECTIVITY; HYDROGENATION; ISOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0037020815 PISSN: 00404020 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4020(02)01189-4 Document Type: Article

Times cited : (25)

References (50)

1
- 0024368157
- (a) Ojima I., Clos N., Bastos C. Tetrahedron. 45:1989;6901.
- (1989) Tetrahedron , vol.45 , pp. 6901
- Ojima, I.¹ Clos, N.² Bastos, C.³

2
- 0001247165
- (b) Noyori R. Acc. Chem. Res. 23:1990;345.
- (1990) Acc. Chem. Res. , vol.23 , pp. 345
- Noyori, R.¹

3
- 37049066528
- (c) Mashima K., Matsumura Y., Kusano K., Kumobayashi H., Sayo N., Hori Y., Ishizaki T., Akutagawa S., Takaya H. J. Chem. Soc., Chem. Commun. 1991;609.
- (1991) J. Chem. Soc., Chem. Commun. , pp. 609
- Mashima, K.¹ Matsumura, Y.² Kusano, K.³ Kumobayashi, H.⁴ Sayo, N.⁵ Hori, Y.⁶ Ishizaki, T.⁷ Akutagawa, S.⁸ Takaya, H.⁹

4
- 0001553672
- Ruzicha L. Helv. Chim. Acta. 9:1926;715.
- (1926) Helv. Chim. Acta , vol.9 , pp. 715
- Ruzicha, L.¹

5
- 11844271601
- For the syntheses of the racemic muscone, see: (a) Tsuji J., Yamada T., Kaito M., Mandai T. Tetrahedron Lett. 22:1979;2257 (b) Tsuji J., Yamada T., Kaito M., Mandai T. Bull. Chem. Soc. Jpn. 53:1980;1417 (c) Suginome H., Yamada S. Tetrahedron Lett. 28:1987;3963 (d) Thies R.W., Daruwala K.P. J. Org. Chem. 52:1987;3798 (e) Ballini R., Marcantoni E., Petrini M. Liebigs Ann. 1995;1381 (f) Wang D.-S., Wang D.-Q., Zhou C.-H. Huaxue Xuebao. 53:1995;909 (g) Takahashi T., Machiba K., Kido Y., Nagashima K., Ebata S., Doi T. Chem. Lett. 1997;1291 (h) Nicolaou K.C., Pastor J., Winssinger N., Murphy F. J. Am. Chem. Soc. 120:1998;5132 (i) Andreas W.-I., Hans J.S., Marianne G. Acta Chem. Scand. 52:1998;672 (j) Kashimura S., Murai Y., Ishifune M., Masuda H., Shimomura M., Murase H., Shono T. Acta Chem. Scand. 53:1999;949 (k) Matthias N., Hans-Jurgen H.H., Georg F. Synlett. 2:2002;275. and the references cited therein.
- (1979) Tetrahedron Lett. , vol.22 , pp. 2257
- Tsuji, J.¹ Yamada, T.² Kaito, M.³ Mandai, T.⁴

6
- 0001006137
- For the syntheses of the racemic muscone, see: (a) Tsuji J., Yamada T., Kaito M., Mandai T. Tetrahedron Lett. 22:1979;2257 (b) Tsuji J., Yamada T., Kaito M., Mandai T. Bull. Chem. Soc. Jpn. 53:1980;1417 (c) Suginome H., Yamada S. Tetrahedron Lett. 28:1987;3963 (d) Thies R.W., Daruwala K.P. J. Org. Chem. 52:1987;3798 (e) Ballini R., Marcantoni E., Petrini M. Liebigs Ann. 1995;1381 (f) Wang D.-S., Wang D.-Q., Zhou C.-H. Huaxue Xuebao. 53:1995;909 (g) Takahashi T., Machiba K., Kido Y., Nagashima K., Ebata S., Doi T. Chem. Lett. 1997;1291 (h) Nicolaou K.C., Pastor J., Winssinger N., Murphy F. J. Am. Chem. Soc. 120:1998;5132 (i) Andreas W.-I., Hans J.S., Marianne G. Acta Chem. Scand. 52:1998;672 (j) Kashimura S., Murai Y., Ishifune M., Masuda H., Shimomura M., Murase H., Shono T. Acta Chem. Scand. 53:1999;949 (k) Matthias N., Hans-Jurgen H.H., Georg F. Synlett. 2:2002;275. and the references cited therein.
- (1980) Bull. Chem. Soc. Jpn , vol.53 , pp. 1417
- Tsuji, J.¹ Yamada, T.² Kaito, M.³ Mandai, T.⁴

7
- 0000785607
- For the syntheses of the racemic muscone, see: (a) Tsuji J., Yamada T., Kaito M., Mandai T. Tetrahedron Lett. 22:1979;2257 (b) Tsuji J., Yamada T., Kaito M., Mandai T. Bull. Chem. Soc. Jpn. 53:1980;1417 (c) Suginome H., Yamada S. Tetrahedron Lett. 28:1987;3963 (d) Thies R.W., Daruwala K.P. J. Org. Chem. 52:1987;3798 (e) Ballini R., Marcantoni E., Petrini M. Liebigs Ann. 1995;1381 (f) Wang D.-S., Wang D.-Q., Zhou C.-H. Huaxue Xuebao. 53:1995;909 (g) Takahashi T., Machiba K., Kido Y., Nagashima K., Ebata S., Doi T. Chem. Lett. 1997;1291 (h) Nicolaou K.C., Pastor J., Winssinger N., Murphy F. J. Am. Chem. Soc. 120:1998;5132 (i) Andreas W.-I., Hans J.S., Marianne G. Acta Chem. Scand. 52:1998;672 (j) Kashimura S., Murai Y., Ishifune M., Masuda H., Shimomura M., Murase H., Shono T. Acta Chem. Scand. 53:1999;949 (k) Matthias N., Hans-Jurgen H.H., Georg F. Synlett. 2:2002;275. and the references cited therein.
- (1987) Tetrahedron Lett. , vol.28 , pp. 3963
- Suginome, H.¹ Yamada, S.²

8
- 0023257840
- For the syntheses of the racemic muscone, see: (a) Tsuji J., Yamada T., Kaito M., Mandai T. Tetrahedron Lett. 22:1979;2257 (b) Tsuji J., Yamada T., Kaito M., Mandai T. Bull. Chem. Soc. Jpn. 53:1980;1417 (c) Suginome H., Yamada S. Tetrahedron Lett. 28:1987;3963 (d) Thies R.W., Daruwala K.P. J. Org. Chem. 52:1987;3798 (e) Ballini R., Marcantoni E., Petrini M. Liebigs Ann. 1995;1381 (f) Wang D.-S., Wang D.-Q., Zhou C.-H. Huaxue Xuebao. 53:1995;909 (g) Takahashi T., Machiba K., Kido Y., Nagashima K., Ebata S., Doi T. Chem. Lett. 1997;1291 (h) Nicolaou K.C., Pastor J., Winssinger N., Murphy F. J. Am. Chem. Soc. 120:1998;5132 (i) Andreas W.-I., Hans J.S., Marianne G. Acta Chem. Scand. 52:1998;672 (j) Kashimura S., Murai Y., Ishifune M., Masuda H., Shimomura M., Murase H., Shono T. Acta Chem. Scand. 53:1999;949 (k) Matthias N., Hans-Jurgen H.H., Georg F. Synlett. 2:2002;275. and the references cited therein.
- (1987) J. Org. Chem. , vol.52 , pp. 3798
- Thies, R.W.¹ Daruwala, K.P.²

9
- 33748886911
- For the syntheses of the racemic muscone, see: (a) Tsuji J., Yamada T., Kaito M., Mandai T. Tetrahedron Lett. 22:1979;2257 (b) Tsuji J., Yamada T., Kaito M., Mandai T. Bull. Chem. Soc. Jpn. 53:1980;1417 (c) Suginome H., Yamada S. Tetrahedron Lett. 28:1987;3963 (d) Thies R.W., Daruwala K.P. J. Org. Chem. 52:1987;3798 (e) Ballini R., Marcantoni E., Petrini M. Liebigs Ann. 1995;1381 (f) Wang D.-S., Wang D.-Q., Zhou C.-H. Huaxue Xuebao. 53:1995;909 (g) Takahashi T., Machiba K., Kido Y., Nagashima K., Ebata S., Doi T. Chem. Lett. 1997;1291 (h) Nicolaou K.C., Pastor J., Winssinger N., Murphy F. J. Am. Chem. Soc. 120:1998;5132 (i) Andreas W.-I., Hans J.S., Marianne G. Acta Chem. Scand. 52:1998;672 (j) Kashimura S., Murai Y., Ishifune M., Masuda H., Shimomura M., Murase H., Shono T. Acta Chem. Scand. 53:1999;949 (k) Matthias N., Hans-Jurgen H.H., Georg F. Synlett. 2:2002;275. and the references cited therein.
- (1995) Liebigs Ann. , pp. 1381
- Ballini, R.¹ Marcantoni, E.² Petrini, M.³

10
- 2942626978
- For the syntheses of the racemic muscone, see: (a) Tsuji J., Yamada T., Kaito M., Mandai T. Tetrahedron Lett. 22:1979;2257 (b) Tsuji J., Yamada T., Kaito M., Mandai T. Bull. Chem. Soc. Jpn. 53:1980;1417 (c) Suginome H., Yamada S. Tetrahedron Lett. 28:1987;3963 (d) Thies R.W., Daruwala K.P. J. Org. Chem. 52:1987;3798 (e) Ballini R., Marcantoni E., Petrini M. Liebigs Ann. 1995;1381 (f) Wang D.-S., Wang D.-Q., Zhou C.-H. Huaxue Xuebao. 53:1995;909 (g) Takahashi T., Machiba K., Kido Y., Nagashima K., Ebata S., Doi T. Chem. Lett. 1997;1291 (h) Nicolaou K.C., Pastor J., Winssinger N., Murphy F. J. Am. Chem. Soc. 120:1998;5132 (i) Andreas W.-I., Hans J.S., Marianne G. Acta Chem. Scand. 52:1998;672 (j) Kashimura S., Murai Y., Ishifune M., Masuda H., Shimomura M., Murase H., Shono T. Acta Chem. Scand. 53:1999;949 (k) Matthias N., Hans-Jurgen H.H., Georg F. Synlett. 2:2002;275. and the references cited therein.
- (1995) Huaxue Xuebao , vol.53 , pp. 909
- Wang, D.-S.¹ Wang, D.-Q.² Zhou, C.-H.³

11
- 0002625378
- For the syntheses of the racemic muscone, see: (a) Tsuji J., Yamada T., Kaito M., Mandai T. Tetrahedron Lett. 22:1979;2257 (b) Tsuji J., Yamada T., Kaito M., Mandai T. Bull. Chem. Soc. Jpn. 53:1980;1417 (c) Suginome H., Yamada S. Tetrahedron Lett. 28:1987;3963 (d) Thies R.W., Daruwala K.P. J. Org. Chem. 52:1987;3798 (e) Ballini R., Marcantoni E., Petrini M. Liebigs Ann. 1995;1381 (f) Wang D.-S., Wang D.-Q., Zhou C.-H. Huaxue Xuebao. 53:1995;909 (g) Takahashi T., Machiba K., Kido Y., Nagashima K., Ebata S., Doi T. Chem. Lett. 1997;1291 (h) Nicolaou K.C., Pastor J., Winssinger N., Murphy F. J. Am. Chem. Soc. 120:1998;5132 (i) Andreas W.-I., Hans J.S., Marianne G. Acta Chem. Scand. 52:1998;672 (j) Kashimura S., Murai Y., Ishifune M., Masuda H., Shimomura M., Murase H., Shono T. Acta Chem. Scand. 53:1999;949 (k) Matthias N., Hans-Jurgen H.H., Georg F. Synlett. 2:2002;275. and the references cited therein.
- (1997) Chem. Lett. , pp. 1291
- Takahashi, T.¹ Machiba, K.² Kido, Y.³ Nagashima, K.⁴ Ebata, S.⁵ Doi, T.⁶

12
- 0032572123
- For the syntheses of the racemic muscone, see: (a) Tsuji J., Yamada T., Kaito M., Mandai T. Tetrahedron Lett. 22:1979;2257 (b) Tsuji J., Yamada T., Kaito M., Mandai T. Bull. Chem. Soc. Jpn. 53:1980;1417 (c) Suginome H., Yamada S. Tetrahedron Lett. 28:1987;3963 (d) Thies R.W., Daruwala K.P. J. Org. Chem. 52:1987;3798 (e) Ballini R., Marcantoni E., Petrini M. Liebigs Ann. 1995;1381 (f) Wang D.-S., Wang D.-Q., Zhou C.-H. Huaxue Xuebao. 53:1995;909 (g) Takahashi T., Machiba K., Kido Y., Nagashima K., Ebata S., Doi T. Chem. Lett. 1997;1291 (h) Nicolaou K.C., Pastor J., Winssinger N., Murphy F. J. Am. Chem. Soc. 120:1998;5132 (i) Andreas W.-I., Hans J.S., Marianne G. Acta Chem. Scand. 52:1998;672 (j) Kashimura S., Murai Y., Ishifune M., Masuda H., Shimomura M., Murase H., Shono T. Acta Chem. Scand. 53:1999;949 (k) Matthias N., Hans-Jurgen H.H., Georg F. Synlett. 2:2002;275. and the references cited therein.
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 5132
- Nicolaou, K.C.¹ Pastor, J.² Winssinger, N.³ Murphy, F.⁴

13
- 0001460609
- For the syntheses of the racemic muscone, see: (a) Tsuji J., Yamada T., Kaito M., Mandai T. Tetrahedron Lett. 22:1979;2257 (b) Tsuji J., Yamada T., Kaito M., Mandai T. Bull. Chem. Soc. Jpn. 53:1980;1417 (c) Suginome H., Yamada S. Tetrahedron Lett. 28:1987;3963 (d) Thies R.W., Daruwala K.P. J. Org. Chem. 52:1987;3798 (e) Ballini R., Marcantoni E., Petrini M. Liebigs Ann. 1995;1381 (f) Wang D.-S., Wang D.-Q., Zhou C.-H. Huaxue Xuebao. 53:1995;909 (g) Takahashi T., Machiba K., Kido Y., Nagashima K., Ebata S., Doi T. Chem. Lett. 1997;1291 (h) Nicolaou K.C., Pastor J., Winssinger N., Murphy F. J. Am. Chem. Soc. 120:1998;5132 (i) Andreas W.-I., Hans J.S., Marianne G. Acta Chem. Scand. 52:1998;672 (j) Kashimura S., Murai Y., Ishifune M., Masuda H., Shimomura M., Murase H., Shono T. Acta Chem. Scand. 53:1999;949 (k) Matthias N., Hans-Jurgen H.H., Georg F. Synlett. 2:2002;275. and the references cited therein.
- (1998) Acta Chem. Scand. , vol.52 , pp. 672
- Andreas, W.-I.¹ Hans, J.S.² Marianne, G.³

14
- 0000381959
- For the syntheses of the racemic muscone, see: (a) Tsuji J., Yamada T., Kaito M., Mandai T. Tetrahedron Lett. 22:1979;2257 (b) Tsuji J., Yamada T., Kaito M., Mandai T. Bull. Chem. Soc. Jpn. 53:1980;1417 (c) Suginome H., Yamada S. Tetrahedron Lett. 28:1987;3963 (d) Thies R.W., Daruwala K.P. J. Org. Chem. 52:1987;3798 (e) Ballini R., Marcantoni E., Petrini M. Liebigs Ann. 1995;1381 (f) Wang D.-S., Wang D.-Q., Zhou C.-H. Huaxue Xuebao. 53:1995;909 (g) Takahashi T., Machiba K., Kido Y., Nagashima K., Ebata S., Doi T. Chem. Lett. 1997;1291 (h) Nicolaou K.C., Pastor J., Winssinger N., Murphy F. J. Am. Chem. Soc. 120:1998;5132 (i) Andreas W.-I., Hans J.S., Marianne G. Acta Chem. Scand. 52:1998;672 (j) Kashimura S., Murai Y., Ishifune M., Masuda H., Shimomura M., Murase H., Shono T. Acta Chem. Scand. 53:1999;949 (k) Matthias N., Hans-Jurgen H.H., Georg F. Synlett. 2:2002;275. and the references cited therein.
- (1999) Acta Chem. Scand. , vol.53 , pp. 949
- Kashimura, S.¹ Murai, Y.² Ishifune, M.³ Masuda, H.⁴ Shimomura, M.⁵ Murase, H.⁶ Shono, T.⁷

15
- 0011162541
- and the references cited therein
- For the syntheses of the racemic muscone, see: (a) Tsuji J., Yamada T., Kaito M., Mandai T. Tetrahedron Lett. 22:1979;2257 (b) Tsuji J., Yamada T., Kaito M., Mandai T. Bull. Chem. Soc. Jpn. 53:1980;1417 (c) Suginome H., Yamada S. Tetrahedron Lett. 28:1987;3963 (d) Thies R.W., Daruwala K.P. J. Org. Chem. 52:1987;3798 (e) Ballini R., Marcantoni E., Petrini M. Liebigs Ann. 1995;1381 (f) Wang D.-S., Wang D.-Q., Zhou C.-H. Huaxue Xuebao. 53:1995;909 (g) Takahashi T., Machiba K., Kido Y., Nagashima K., Ebata S., Doi T. Chem. Lett. 1997;1291 (h) Nicolaou K.C., Pastor J., Winssinger N., Murphy F. J. Am. Chem. Soc. 120:1998;5132 (i) Andreas W.-I., Hans J.S., Marianne G. Acta Chem. Scand. 52:1998;672 (j) Kashimura S., Murai Y., Ishifune M., Masuda H., Shimomura M., Murase H., Shono T. Acta Chem. Scand. 53:1999;949 (k) Matthias N., Hans-Jurgen H.H., Georg F. Synlett. 2:2002;275. and the references cited therein.
- (2002) Synlett , vol.2 , pp. 275
- Matthias, N.¹ Hans-Jurgen, H.H.² Georg, F.³

16
- 0000417977
- For the syntheses of the optically active muscone, see: (a) Mamdapur V.R., Pai P.P., Chakravari K.K., Nayak U.G., Bhattacharyya S.C. Tetrahedron. 20:1964;2601 (b) Branca Q., Fischli A. Helv. Chim. Acta. 60:1977;925 (c) Utimoto K., Tanaka M., Kitai M., Nozaki H. Tetrahedron Lett. 26:1978;2301 (d) Abad A., Amo M., Pardo A., Pedro J.R., Seoane E. Chem. Ind. 1985;29 (e) Terunuma D., Motegi M., Tsuda M., Sawada T., Nozawa H., Nohira H. J. Org. Chem. 52:1987;1630 (f) Xie Z.-F., Suemune H., Sakai K. J. Chem. Soc., Chem. Commun. 1988;1638 (g) Dowd P., Choi S.C. Tetrahedron. 48:1992;4773 (h) Kamat V.P., Hagiwara H., Suzuki T., Ando M. J. Chem. Soc., Perkin Trans. 1. 1998;2253 (i) Kamat V.P., Hagiwara H., Katsumi H., Hoshi T., Suzuki T., Ando M. Tetrahedron. 56:2000;4397.
- (1964) Tetrahedron , vol.20 , pp. 2601
- Mamdapur, V.R.¹ Pai, P.P.² Chakravari, K.K.³ Nayak, U.G.⁴ Bhattacharyya, S.C.⁵

17
- 84963184494
- For the syntheses of the optically active muscone, see: (a) Mamdapur V.R., Pai P.P., Chakravari K.K., Nayak U.G., Bhattacharyya S.C. Tetrahedron. 20:1964;2601 (b) Branca Q., Fischli A. Helv. Chim. Acta. 60:1977;925 (c) Utimoto K., Tanaka M., Kitai M., Nozaki H. Tetrahedron Lett. 26:1978;2301 (d) Abad A., Amo M., Pardo A., Pedro J.R., Seoane E. Chem. Ind. 1985;29 (e) Terunuma D., Motegi M., Tsuda M., Sawada T., Nozawa H., Nohira H. J. Org. Chem. 52:1987;1630 (f) Xie Z.-F., Suemune H., Sakai K. J. Chem. Soc., Chem. Commun. 1988;1638 (g) Dowd P., Choi S.C. Tetrahedron. 48:1992;4773 (h) Kamat V.P., Hagiwara H., Suzuki T., Ando M. J. Chem. Soc., Perkin Trans. 1. 1998;2253 (i) Kamat V.P., Hagiwara H., Katsumi H., Hoshi T., Suzuki T., Ando M. Tetrahedron. 56:2000;4397.
- (1977) Helv. Chim. Acta , vol.60 , pp. 925
- Branca, Q.¹ Fischli, A.²

18
- 0001856918
- For the syntheses of the optically active muscone, see: (a) Mamdapur V.R., Pai P.P., Chakravari K.K., Nayak U.G., Bhattacharyya S.C. Tetrahedron. 20:1964;2601 (b) Branca Q., Fischli A. Helv. Chim. Acta. 60:1977;925 (c) Utimoto K., Tanaka M., Kitai M., Nozaki H. Tetrahedron Lett. 26:1978;2301 (d) Abad A., Amo M., Pardo A., Pedro J.R., Seoane E. Chem. Ind. 1985;29 (e) Terunuma D., Motegi M., Tsuda M., Sawada T., Nozawa H., Nohira H. J. Org. Chem. 52:1987;1630 (f) Xie Z.-F., Suemune H., Sakai K. J. Chem. Soc., Chem. Commun. 1988;1638 (g) Dowd P., Choi S.C. Tetrahedron. 48:1992;4773 (h) Kamat V.P., Hagiwara H., Suzuki T., Ando M. J. Chem. Soc., Perkin Trans. 1. 1998;2253 (i) Kamat V.P., Hagiwara H., Katsumi H., Hoshi T., Suzuki T., Ando M. Tetrahedron. 56:2000;4397.
- (1978) Tetrahedron Lett. , vol.26 , pp. 2301
- Utimoto, K.¹ Tanaka, M.² Kitai, M.³ Nozaki, H.⁴

19
- 26444533063
- For the syntheses of the optically active muscone, see: (a) Mamdapur V.R., Pai P.P., Chakravari K.K., Nayak U.G., Bhattacharyya S.C. Tetrahedron. 20:1964;2601 (b) Branca Q., Fischli A. Helv. Chim. Acta. 60:1977;925 (c) Utimoto K., Tanaka M., Kitai M., Nozaki H. Tetrahedron Lett. 26:1978;2301 (d) Abad A., Amo M., Pardo A., Pedro J.R., Seoane E. Chem. Ind. 1985;29 (e) Terunuma D., Motegi M., Tsuda M., Sawada T., Nozawa H., Nohira H. J. Org. Chem. 52:1987;1630 (f) Xie Z.-F., Suemune H., Sakai K. J. Chem. Soc., Chem. Commun. 1988;1638 (g) Dowd P., Choi S.C. Tetrahedron. 48:1992;4773 (h) Kamat V.P., Hagiwara H., Suzuki T., Ando M. J. Chem. Soc., Perkin Trans. 1. 1998;2253 (i) Kamat V.P., Hagiwara H., Katsumi H., Hoshi T., Suzuki T., Ando M. Tetrahedron. 56:2000;4397.
- (1985) Chem. Ind. , pp. 29
- Abad, A.¹ Amo, M.² Pardo, A.³ Pedro, J.R.⁴ Seoane, E.⁵

20
- 0001412843
- For the syntheses of the optically active muscone, see: (a) Mamdapur V.R., Pai P.P., Chakravari K.K., Nayak U.G., Bhattacharyya S.C. Tetrahedron. 20:1964;2601 (b) Branca Q., Fischli A. Helv. Chim. Acta. 60:1977;925 (c) Utimoto K., Tanaka M., Kitai M., Nozaki H. Tetrahedron Lett. 26:1978;2301 (d) Abad A., Amo M., Pardo A., Pedro J.R., Seoane E. Chem. Ind. 1985;29 (e) Terunuma D., Motegi M., Tsuda M., Sawada T., Nozawa H., Nohira H. J. Org. Chem. 52:1987;1630 (f) Xie Z.-F., Suemune H., Sakai K. J. Chem. Soc., Chem. Commun. 1988;1638 (g) Dowd P., Choi S.C. Tetrahedron. 48:1992;4773 (h) Kamat V.P., Hagiwara H., Suzuki T., Ando M. J. Chem. Soc., Perkin Trans. 1. 1998;2253 (i) Kamat V.P., Hagiwara H., Katsumi H., Hoshi T., Suzuki T., Ando M. Tetrahedron. 56:2000;4397.
- (1987) J. Org. Chem. , vol.52 , pp. 1630
- Terunuma, D.¹ Motegi, M.² Tsuda, M.³ Sawada, T.⁴ Nozawa, H.⁵ Nohira, H.⁶

21
- 0024231082
- For the syntheses of the optically active muscone, see: (a) Mamdapur V.R., Pai P.P., Chakravari K.K., Nayak U.G., Bhattacharyya S.C. Tetrahedron. 20:1964;2601 (b) Branca Q., Fischli A. Helv. Chim. Acta. 60:1977;925 (c) Utimoto K., Tanaka M., Kitai M., Nozaki H. Tetrahedron Lett. 26:1978;2301 (d) Abad A., Amo M., Pardo A., Pedro J.R., Seoane E. Chem. Ind. 1985;29 (e) Terunuma D., Motegi M., Tsuda M., Sawada T., Nozawa H., Nohira H. J. Org. Chem. 52:1987;1630 (f) Xie Z.-F., Suemune H., Sakai K. J. Chem. Soc., Chem. Commun. 1988;1638 (g) Dowd P., Choi S.C. Tetrahedron. 48:1992;4773 (h) Kamat V.P., Hagiwara H., Suzuki T., Ando M. J. Chem. Soc., Perkin Trans. 1. 1998;2253 (i) Kamat V.P., Hagiwara H., Katsumi H., Hoshi T., Suzuki T., Ando M. Tetrahedron. 56:2000;4397.
- (1988) J. Chem. Soc., Chem. Commun. , pp. 1638
- Xie, Z.-F.¹ Suemune, H.² Sakai, K.³

22
- 0026764279
- For the syntheses of the optically active muscone, see: (a) Mamdapur V.R., Pai P.P., Chakravari K.K., Nayak U.G., Bhattacharyya S.C. Tetrahedron. 20:1964;2601 (b) Branca Q., Fischli A. Helv. Chim. Acta. 60:1977;925 (c) Utimoto K., Tanaka M., Kitai M., Nozaki H. Tetrahedron Lett. 26:1978;2301 (d) Abad A., Amo M., Pardo A., Pedro J.R., Seoane E. Chem. Ind. 1985;29 (e) Terunuma D., Motegi M., Tsuda M., Sawada T., Nozawa H., Nohira H. J. Org. Chem. 52:1987;1630 (f) Xie Z.-F., Suemune H., Sakai K. J. Chem. Soc., Chem. Commun. 1988;1638 (g) Dowd P., Choi S.C. Tetrahedron. 48:1992;4773 (h) Kamat V.P., Hagiwara H., Suzuki T., Ando M. J. Chem. Soc., Perkin Trans. 1. 1998;2253 (i) Kamat V.P., Hagiwara H., Katsumi H., Hoshi T., Suzuki T., Ando M. Tetrahedron. 56:2000;4397.
- (1992) Tetrahedron , vol.48 , pp. 4773
- Dowd, P.¹ Choi, S.C.²

23
- 33748722780
- For the syntheses of the optically active muscone, see: (a) Mamdapur V.R., Pai P.P., Chakravari K.K., Nayak U.G., Bhattacharyya S.C. Tetrahedron. 20:1964;2601 (b) Branca Q., Fischli A. Helv. Chim. Acta. 60:1977;925 (c) Utimoto K., Tanaka M., Kitai M., Nozaki H. Tetrahedron Lett. 26:1978;2301 (d) Abad A., Amo M., Pardo A., Pedro J.R., Seoane E. Chem. Ind. 1985;29 (e) Terunuma D., Motegi M., Tsuda M., Sawada T., Nozawa H., Nohira H. J. Org. Chem. 52:1987;1630 (f) Xie Z.-F., Suemune H., Sakai K. J. Chem. Soc., Chem. Commun. 1988;1638 (g) Dowd P., Choi S.C. Tetrahedron. 48:1992;4773 (h) Kamat V.P., Hagiwara H., Suzuki T., Ando M. J. Chem. Soc., Perkin Trans. 1. 1998;2253 (i) Kamat V.P., Hagiwara H., Katsumi H., Hoshi T., Suzuki T., Ando M. Tetrahedron. 56:2000;4397.
- (1998) J. Chem. Soc., Perkin Trans. 1 , pp. 2253
- Kamat, V.P.¹ Hagiwara, H.² Suzuki, T.³ Ando, M.⁴

24
- 0034705481
- For the syntheses of the optically active muscone, see: (a) Mamdapur V.R., Pai P.P., Chakravari K.K., Nayak U.G., Bhattacharyya S.C. Tetrahedron. 20:1964;2601 (b) Branca Q., Fischli A. Helv. Chim. Acta. 60:1977;925 (c) Utimoto K., Tanaka M., Kitai M., Nozaki H. Tetrahedron Lett. 26:1978;2301 (d) Abad A., Amo M., Pardo A., Pedro J.R., Seoane E. Chem. Ind. 1985;29 (e) Terunuma D., Motegi M., Tsuda M., Sawada T., Nozawa H., Nohira H. J. Org. Chem. 52:1987;1630 (f) Xie Z.-F., Suemune H., Sakai K. J. Chem. Soc., Chem. Commun. 1988;1638 (g) Dowd P., Choi S.C. Tetrahedron. 48:1992;4773 (h) Kamat V.P., Hagiwara H., Suzuki T., Ando M. J. Chem. Soc., Perkin Trans. 1. 1998;2253 (i) Kamat V.P., Hagiwara H., Katsumi H., Hoshi T., Suzuki T., Ando M. Tetrahedron. 56:2000;4397.
- (2000) Tetrahedron , vol.56 , pp. 4397
- Kamat, V.P.¹ Hagiwara, H.² Katsumi, H.³ Hoshi, T.⁴ Suzuki, T.⁵ Ando, M.⁶

25
- 26444609824
- (a) Tanaka K., Ushio H., Suzuki H. J. Chem. Soc., Chem. Commun. 1990;795.
- (1990) J. Chem. Soc., Chem. Commun. , pp. 795
- Tanaka, K.¹ Ushio, H.² Suzuki, H.³

26
- 26444502832
- (b) Tanaka K., Suzuki H. J. Chem. Soc., Chem. Commun. 1991;101.
- (1991) J. Chem. Soc., Chem. Commun. , pp. 101
- Tanaka, K.¹ Suzuki, H.²

27
- 0011201286
- (c) Ogura T., Fang C.L., Suemune H., Sakai K. J. Chem. Soc., Chem. Commun. 1991;1438.
- (1991) J. Chem. Soc., Chem. Commun. , pp. 1438
- Ogura, T.¹ Fang, C.L.² Suemune, H.³ Sakai, K.⁴

28
- 37049083559
- (d) Tanaka K., Matsui J., Suzuki H., Watanabe A. J. Chem. Soc., Perkin Trans. 1. 1991;1445.
- (1991) J. Chem. Soc., Perkin Trans. 1 , pp. 1445
- Tanaka, K.¹ Matsui, J.² Suzuki, H.³ Watanabe, A.⁴

29
- 84992255084
- (e) Tanaka K., Uchino H., Kawabata Y., Suzuki H. J. Chem. Soc., Perkin Trans. 1. 1992;1193.
- (1992) J. Chem. Soc., Perkin Trans. 1 , pp. 1193
- Tanaka, K.¹ Uchino, H.² Kawabata, Y.³ Suzuki, H.⁴

30
- 37049074156
- (f) Tanaka K., Matsui J., Suzuki H. J. Chem. Soc., Perkin Trans. 1. 1993;157.
- (1993) J. Chem. Soc., Perkin Trans. 1 , pp. 157
- Tanaka, K.¹ Matsui, J.² Suzuki, H.³

31
- 84944646622
- (g) Tanaka K., Matsui J., Somemiya K. Synlett. 1994;351.
- (1994) Synlett , pp. 351
- Tanaka, K.¹ Matsui, J.² Somemiya, K.³

32
- 0343967492
- (h) Yamaguchi M., Shiraishi T., Hirama M. J. Org. Chem. 61:1996;3520.
- (1996) J. Org. Chem. , vol.61 , pp. 3520
- Yamaguchi, M.¹ Shiraishi, T.² Hirama, M.³

33
- 0032723513
- (i) Alexakis A., Benhaim C., Fournious X., van der Heuvel A., Leveque J.-M., March S. Synlett. 1999;1811.
- (1999) Synlett , pp. 1811
- Alexakis, A.¹ Benhaim, C.² Fournious, X.³ Van der Heuvel, A.⁴ Leveque, J.-M.⁵ March, S.⁶

34
- 33845374391
- (a) Nelson K.A., Mash E.A. J. Org. Chem. 51:1986;2721.
- (1986) J. Org. Chem. , vol.51 , pp. 2721
- Nelson, K.A.¹ Mash, E.A.²

35
- 0011167084
- (b) Xie B.H., Lu S.J., Gao L., Fu H.X. Fenzi Cuihua. 11:1997;433.
- (1997) Fenzi Cuihua , vol.11 , pp. 433
- Xie, B.H.¹ Lu, S.J.² Gao, L.³ Fu, H.X.⁴

36
- 0001730323
- (c) Xie B.H., Lu S.J., Fu H.X., Gao L. Chin. Chem. Lett. 8:1997;477.
- (1997) Chin. Chem. Lett. , vol.8 , pp. 477
- Xie, B.H.¹ Lu, S.J.² Fu, H.X.³ Gao, L.⁴

37
- 0026501690
- Ohta T., Miyake T., Seido N., Kumobayashi H., Akutagawa S., Takaya H. Tetrahedron Lett. 33:1992;635.
- (1992) Tetrahedron Lett. , vol.33 , pp. 635
- Ohta, T.¹ Miyake, T.² Seido, N.³ Kumobayashi, H.⁴ Akutagawa, S.⁵ Takaya, H.⁶

38
- 0001757410
- Brunner H., Leitner W. J. Organomet. Chem. 387:1990;209.
- (1990) J. Organomet. Chem. , vol.387 , pp. 209
- Brunner, H.¹ Leitner, W.²

39
- 0004114852
- Swift A.D. Karl. Dordrecht: Kluwer Academic
- A part of the present work have been published in: Swift, Karl A.D., Current Topics in Flavours and Fragrances. 1999;33 Kluwer Academic, Dordrecht.
- (1999) Current Topics in Flavours and Fragrances , pp. 33

40
- 84925293896
- Stoll M., Rouve A. Helv. Chim. Acta. 30:1947;2019.
- (1947) Helv. Chim. Acta , vol.30 , pp. 2019
- Stoll, M.¹ Rouve, A.²

41
- 0011194751
- Wangzhong C., Kefang J. Huaxue Tongbao. 1998;44.
- (1998) Huaxue Tongbao , pp. 44
- Wangzhong, C.¹ Kefang, J.²

42
- 0037037849
- Tanabe, Y.; Matsumoto, N.; Higashi, T.; Misaki, T.; Itoh, T.; Yamamoto, M.; Mitarai, K.; Nishi, Y. Tetrahedron, 2002, 58, 8269.
- (2002) Tetrahedron , vol.58 , pp. 8269
- Tanabe, Y.¹ Matsumoto, N.² Higashi, T.³ Misaki, T.⁴ Itoh, T.⁵ Yamamoto, M.⁶ Mitarai, K.⁷ Nishi, Y.⁸

43
- 0031539860
- (a) Chen H.S., Liu X.F., Xu H.S. Chin. Chem. Lett. 8:1997;17.
- (1997) Chin. Chem. Lett. , vol.8 , pp. 17
- Chen, H.S.¹ Liu, X.F.² Xu, H.S.³

44
- 0011166811
- (b) Yinjuan B., Jun L., Zhen S., Binggen Y. Synlett. 2001;544.
- (2001) Synlett , pp. 544
- Yinjuan, B.¹ Jun, L.² Zhen, S.³ Binggen, Y.⁴

45
- 26044439756
- see also p 4
- David M., Ken P. Perfumer Flavorist. 25:(3):2000;1-2. see also p 4.
- (2000) Perfumer Flavorist , vol.25 , Issue.3 , pp. 1-2
- David, M.¹ Ken, P.²

46
- 37049095109
- Ikariya T., Ishii Y., Kawano H., Arai T., Saburi M., Yoshikawa S., Akutagawa S. J. Chem. Soc., Chem. Commun. 1985;922.
- (1985) J. Chem. Soc., Chem. Commun. , pp. 922
- Ikariya, T.¹ Ishii, Y.² Kawano, H.³ Arai, T.⁴ Saburi, M.⁵ Yoshikawa, S.⁶ Akutagawa, S.⁷

47
- 33845278799
- Ohta T., Takaya H., Noyori R. Inorg. Chem. 27:1988;566.
- (1988) Inorg. Chem. , vol.27 , pp. 566
- Ohta, T.¹ Takaya, H.² Noyori, R.³

48
- 37049066528
- Mashima K., Matsumura Y., Kusano K., Kumobayashi H., Sayo N., Hori Y., Ishizaki T., Akutagawa S., Takaya H. J. Chem. Soc., Chem. Commun. 1991;609.
- (1991) J. Chem. Soc., Chem. Commun. , pp. 609
- Mashima, K.¹ Matsumura, Y.² Kusano, K.³ Kumobayashi, H.⁴ Sayo, N.⁵ Hori, Y.⁶ Ishizaki, T.⁷ Akutagawa, S.⁸ Takaya, H.⁹

49
- 33845281684
- Takaya H., Ohta T., Sayo N., Kumobayashi H., Akutagawa S., Inoue S., Kasahara I., Noyori R. J. Am. Chem. Soc. 109:1987;1956.
- (1987) J. Am. Chem. Soc. , vol.109 , pp. 1956
- Takaya, H.¹ Ohta, T.² Sayo, N.³ Kumobayashi, H.⁴ Akutagawa, S.⁵ Inoue, S.⁶ Kasahara, I.⁷ Noyori, R.⁸

50
- 0011225940
- Stoll M. Helv. Chim. Acta. 34:1951;1817.
- (1951) Helv. Chim. Acta , vol.34 , pp. 1817
- Stoll, M.¹

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