SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 7, 2004, Pages 1211-1214

An enantioselective total synthesis of (-)-stemoamide

(2) Sibi, Mukund P a Subramanian, Thangaiah a

a NORTH DAKOTA STATE UNIVERSITY (United States)

Author keywords

Conjugate addition; Pyroglutamic acid; Ring closing metathesis; Stemoamide

Indexed keywords

ALCOHOL DERIVATIVE; AMIDE; PYROGLUTAMYL ALCOHOL; STEMOAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CONJUGATION; DRUG SYNTHESIS; ENANTIOSELECTIVITY; RING CLOSING METATHESIS;

EID: 2942746702 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2004-822927 Document Type: Article

Times cited : (43)

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- For conjugate addition to γ-amino alkenoates with varied levels of syn selectivity see: (a) Moriwake, T.; Hamano, S.; Saito, S. Heterocycles 1988, 27, 1135. (b) Le Coz, S.; Mann, A.; Thareau, P.; Taddei, M. Heterocycles 1993, 36, 2073. (c) Reetz, M. T.; Röhrig, D. Angew. Chem., Int. Ed. Engl. 1989, 28, 1706. (d) Jako, I.; Uiber, P.; Mann, A.; Taddei, M.; Wermuth, C. G. Tetrahedron Lett. 1990, 31, 1011. (e) Jako, I.; Uiber, P.; Mann, A.; Wermuth, C. G.; Boulanger, T.; Norberg, B.; Evrard, G.; Durant, F. J. Org. Chem. 1991, 56, 5729. (f) Hanessian, S.; Sumi, K. Synthesis 1991, 1083. (g) Hanessian, S.; Demont, E.; van Otterlo, W. A. L. Tetrahedron Lett. 2000, 41, 4999. (h) Hanessian, S.; Wang, W.; Gai, Y. Tetrahedron Lett. 1996, 37, 7477. (i) Paz, M. M.; Sardina, F. J. J. Org. Chem. 1993, 58, 6990.
- (1991) Synthesis , pp. 1083
- Hanessian, S.¹ Sumi, K.²

41
- 0034709568
- For conjugate addition to γ-amino alkenoates with varied levels of syn selectivity see: (a) Moriwake, T.; Hamano, S.; Saito, S. Heterocycles 1988, 27, 1135. (b) Le Coz, S.; Mann, A.; Thareau, P.; Taddei, M. Heterocycles 1993, 36, 2073. (c) Reetz, M. T.; Röhrig, D. Angew. Chem., Int. Ed. Engl. 1989, 28, 1706. (d) Jako, I.; Uiber, P.; Mann, A.; Taddei, M.; Wermuth, C. G. Tetrahedron Lett. 1990, 31, 1011. (e) Jako, I.; Uiber, P.; Mann, A.; Wermuth, C. G.; Boulanger, T.; Norberg, B.; Evrard, G.; Durant, F. J. Org. Chem. 1991, 56, 5729. (f) Hanessian, S.; Sumi, K. Synthesis 1991, 1083. (g) Hanessian, S.; Demont, E.; van Otterlo, W. A. L. Tetrahedron Lett. 2000, 41, 4999. (h) Hanessian, S.; Wang, W.; Gai, Y. Tetrahedron Lett. 1996, 37, 7477. (i) Paz, M. M.; Sardina, F. J. J. Org. Chem. 1993, 58, 6990.
- (2000) Tetrahedron Lett. , vol.41 , pp. 4999
- Hanessian, S.¹ Demont, E.² Van Otterlo, W.A.L.³

42
- 0030583508
- For conjugate addition to γ-amino alkenoates with varied levels of syn selectivity see: (a) Moriwake, T.; Hamano, S.; Saito, S. Heterocycles 1988, 27, 1135. (b) Le Coz, S.; Mann, A.; Thareau, P.; Taddei, M. Heterocycles 1993, 36, 2073. (c) Reetz, M. T.; Röhrig, D. Angew. Chem., Int. Ed. Engl. 1989, 28, 1706. (d) Jako, I.; Uiber, P.; Mann, A.; Taddei, M.; Wermuth, C. G. Tetrahedron Lett. 1990, 31, 1011. (e) Jako, I.; Uiber, P.; Mann, A.; Wermuth, C. G.; Boulanger, T.; Norberg, B.; Evrard, G.; Durant, F. J. Org. Chem. 1991, 56, 5729. (f) Hanessian, S.; Sumi, K. Synthesis 1991, 1083. (g) Hanessian, S.; Demont, E.; van Otterlo, W. A. L. Tetrahedron Lett. 2000, 41, 4999. (h) Hanessian, S.; Wang, W.; Gai, Y. Tetrahedron Lett. 1996, 37, 7477. (i) Paz, M. M.; Sardina, F. J. J. Org. Chem. 1993, 58, 6990.
- (1996) Tetrahedron Lett. , vol.37 , pp. 7477
- Hanessian, S.¹ Wang, W.² Gai, Y.³

43
- 0000085892
- For conjugate addition to γ-amino alkenoates with varied levels of syn selectivity see: (a) Moriwake, T.; Hamano, S.; Saito, S. Heterocycles 1988, 27, 1135. (b) Le Coz, S.; Mann, A.; Thareau, P.; Taddei, M. Heterocycles 1993, 36, 2073. (c) Reetz, M. T.; Röhrig, D. Angew. Chem., Int. Ed. Engl. 1989, 28, 1706. (d) Jako, I.; Uiber, P.; Mann, A.; Taddei, M.; Wermuth, C. G. Tetrahedron Lett. 1990, 31, 1011. (e) Jako, I.; Uiber, P.; Mann, A.; Wermuth, C. G.; Boulanger, T.; Norberg, B.; Evrard, G.; Durant, F. J. Org. Chem. 1991, 56, 5729. (f) Hanessian, S.; Sumi, K. Synthesis 1991, 1083. (g) Hanessian, S.; Demont, E.; van Otterlo, W. A. L. Tetrahedron Lett. 2000, 41, 4999. (h) Hanessian, S.; Wang, W.; Gai, Y. Tetrahedron Lett. 1996, 37, 7477. (i) Paz, M. M.; Sardina, F. J. J. Org. Chem. 1993, 58, 6990.
- (1993) J. Org. Chem. , vol.58 , pp. 6990
- Paz, M.M.¹ Sardina, F.J.²

44
- 0001562620
- For examples of highly diastereoselective conjugate additions of copper reagents to γ-substituted alkenoates and discussions on stereoselectivity in these reactions see: (a) Yamamoto, Y.; Chounan, Y.; Nishii, S.; Ibuka, T.; Kitahara, H. J. Am. Chem. Soc. 1992, 114, 7652. (b) Roush, W. R.; Lesur, B. M. Tetrahedron Lett. 1983, 24, 2231. (c) Roush, W. R.; Michaelides, M. R.; Tai, D. F.; Lesur, B. M.; Chong, W. K. M.; Harris, D. J. J. Am. Chem. Soc. 1989, 111, 2984.
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 7652
- Yamamoto, Y.¹ Chounan, Y.² Nishii, S.³ Ibuka, T.⁴ Kitahara, H.⁵

45
- 0001592452
- For examples of highly diastereoselective conjugate additions of copper reagents to γ-substituted alkenoates and discussions on stereoselectivity in these reactions see: (a) Yamamoto, Y.; Chounan, Y.; Nishii, S.; Ibuka, T.; Kitahara, H. J. Am. Chem. Soc. 1992, 114, 7652. (b) Roush, W. R.; Lesur, B. M. Tetrahedron Lett. 1983, 24, 2231. (c) Roush, W. R.; Michaelides, M. R.; Tai, D. F.; Lesur, B. M.; Chong, W. K. M.; Harris, D. J. J. Am. Chem. Soc. 1989, 111, 2984.
- (1983) Tetrahedron Lett. , vol.24 , pp. 2231
- Roush, W.R.¹ Lesur, B.M.²

46
- 0024583912
- For examples of highly diastereoselective conjugate additions of copper reagents to γ-substituted alkenoates and discussions on stereoselectivity in these reactions see: (a) Yamamoto, Y.; Chounan, Y.; Nishii, S.; Ibuka, T.; Kitahara, H. J. Am. Chem. Soc. 1992, 114, 7652. (b) Roush, W. R.; Lesur, B. M. Tetrahedron Lett. 1983, 24, 2231. (c) Roush, W. R.; Michaelides, M. R.; Tai, D. F.; Lesur, B. M.; Chong, W. K. M.; Harris, D. J. J. Am. Chem. Soc. 1989, 111, 2984.
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 2984
- Roush, W.R.¹ Michaelides, M.R.² Tai, D.F.³ Lesur, B.M.⁴ Chong, W.K.M.⁵ Harris, D.J.⁶

47
- 2942703294
- note
- +: 274.1413; found: 274.1410. The stereochemistry at C-9 was unambiguously established at a later stage (compounds 15 and 17).

48
- 2942738348
- note
- Interestingly, conjugate addition to the corresponding Z-ester gave a 2:1 mixture of diastereomers with 7 as the major product (data not shown).

49
- 0034746687
- (a) For recent reviews on ring-closing metathesis see: Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
- (2001) Acc. Chem. Res. , vol.34 , pp. 18
- Trnka, T.M.¹ Grubbs, R.H.²

50
- 0344006321
- (b) Also see: Fürstner, A. Angew. Chem. Int. Ed. 2000, 39, 3012.
- (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 3012
- Fürstner, A.¹

51
- 0000508498
- For the formation of 7-membered azacycles using RCM see the following: (c) Turling, C. A.; Holmes, A. B.; Markwell, R. E.; Pearson, N. D. J. Chem. Soc., Perkin Trans. 1 1999, 1695. (d) Barrett, A. G. M.; Ahmed, M.; Baker, S. P.; Baugh, S. P. D.; Braddock, D. C.; Procopiou, P. A.; White, A. J. P.; Williams, D. J. J. Org. Chem. 2000, 65, 3716. (e) Martin, S. F.; Chen, H.-J.; Courtney, A. K.; Liao, Y.; Pätzel, M.; Ramser, M. N.; Wagman, A. S. Tetrahedron 1996, 52, 7251. (f) Colombo, L.; Di Giacomo, M.; Vinci, V.; Colombo, M.; Manzoni, L.; Scolastico, C. Tetrahedron 2003, 59, 4501. (g) Vo-Thanh, G.; Boucard, V.; Sauriat-Dorizon, H.; Guibe, F. Synlett 2001, 37. (h) Lim, S. H.; Ma, S.; Beak, P. J. Org. Chem. 2001, 66, 9056. (i) Beal, L. M.; Liu, B.; Chu, W.; Moeller, K. D. Tetrahedron 2000, 56, 10113. (j) Hoffmann, T.; Lanig, H.; Waibel, R.; Gmeiner, P. Angew. Chem. Int. Ed. 2001, 40, 3361. (k) Grossmith, C. E.; Senia, F.; Wagner, J. Synlett 1999, 1660.
- (1999) J. Chem. Soc., Perkin Trans. 1 , pp. 1695
- Turling, C.A.¹ Holmes, A.B.² Markwell, R.E.³ Pearson, N.D.⁴

52
- 0034674463
- For the formation of 7-membered azacycles using RCM see the following: (c) Turling, C. A.; Holmes, A. B.; Markwell, R. E.; Pearson, N. D. J. Chem. Soc., Perkin Trans. 1 1999, 1695. (d) Barrett, A. G. M.; Ahmed, M.; Baker, S. P.; Baugh, S. P. D.; Braddock, D. C.; Procopiou, P. A.; White, A. J. P.; Williams, D. J. J. Org. Chem. 2000, 65, 3716. (e) Martin, S. F.; Chen, H.-J.; Courtney, A. K.; Liao, Y.; Pätzel, M.; Ramser, M. N.; Wagman, A. S. Tetrahedron 1996, 52, 7251. (f) Colombo, L.; Di Giacomo, M.; Vinci, V.; Colombo, M.; Manzoni, L.; Scolastico, C. Tetrahedron 2003, 59, 4501. (g) Vo-Thanh, G.; Boucard, V.; Sauriat-Dorizon, H.; Guibe, F. Synlett 2001, 37. (h) Lim, S. H.; Ma, S.; Beak, P. J. Org. Chem. 2001, 66, 9056. (i) Beal, L. M.; Liu, B.; Chu, W.; Moeller, K. D. Tetrahedron 2000, 56, 10113. (j) Hoffmann, T.; Lanig, H.; Waibel, R.; Gmeiner, P. Angew. Chem. Int. Ed. 2001, 40, 3361. (k) Grossmith, C. E.; Senia, F.; Wagner, J. Synlett 1999, 1660.
- (2000) J. Org. Chem. , vol.65 , pp. 3716
- Barrett, A.G.M.¹ Ahmed, M.² Baker, S.P.³ Baugh, S.P.D.⁴ Braddock, D.C.⁵ Procopiou, P.A.⁶ White, A.J.P.⁷ Williams, D.J.⁸

53
- 0029870160
- For the formation of 7-membered azacycles using RCM see the following: (c) Turling, C. A.; Holmes, A. B.; Markwell, R. E.; Pearson, N. D. J. Chem. Soc., Perkin Trans. 1 1999, 1695. (d) Barrett, A. G. M.; Ahmed, M.; Baker, S. P.; Baugh, S. P. D.; Braddock, D. C.; Procopiou, P. A.; White, A. J. P.; Williams, D. J. J. Org. Chem. 2000, 65, 3716. (e) Martin, S. F.; Chen, H.-J.; Courtney, A. K.; Liao, Y.; Pätzel, M.; Ramser, M. N.; Wagman, A. S. Tetrahedron 1996, 52, 7251. (f) Colombo, L.; Di Giacomo, M.; Vinci, V.; Colombo, M.; Manzoni, L.; Scolastico, C. Tetrahedron 2003, 59, 4501. (g) Vo-Thanh, G.; Boucard, V.; Sauriat-Dorizon, H.; Guibe, F. Synlett 2001, 37. (h) Lim, S. H.; Ma, S.; Beak, P. J. Org. Chem. 2001, 66, 9056. (i) Beal, L. M.; Liu, B.; Chu, W.; Moeller, K. D. Tetrahedron 2000, 56, 10113. (j) Hoffmann, T.; Lanig, H.; Waibel, R.; Gmeiner, P. Angew. Chem. Int. Ed. 2001, 40, 3361. (k) Grossmith, C. E.; Senia, F.; Wagner, J. Synlett 1999, 1660.
- (1996) Tetrahedron , vol.52 , pp. 7251
- Martin, S.F.¹ Chen, H.-J.² Courtney, A.K.³ Liao, Y.⁴ Pätzel, M.⁵ Ramser, M.N.⁶ Wagman, A.S.⁷

54
- 0037498265
- For the formation of 7-membered azacycles using RCM see the following: (c) Turling, C. A.; Holmes, A. B.; Markwell, R. E.; Pearson, N. D. J. Chem. Soc., Perkin Trans. 1 1999, 1695. (d) Barrett, A. G. M.; Ahmed, M.; Baker, S. P.; Baugh, S. P. D.; Braddock, D. C.; Procopiou, P. A.; White, A. J. P.; Williams, D. J. J. Org. Chem. 2000, 65, 3716. (e) Martin, S. F.; Chen, H.-J.; Courtney, A. K.; Liao, Y.; Pätzel, M.; Ramser, M. N.; Wagman, A. S. Tetrahedron 1996, 52, 7251. (f) Colombo, L.; Di Giacomo, M.; Vinci, V.; Colombo, M.; Manzoni, L.; Scolastico, C. Tetrahedron 2003, 59, 4501. (g) Vo-Thanh, G.; Boucard, V.; Sauriat-Dorizon, H.; Guibe, F. Synlett 2001, 37. (h) Lim, S. H.; Ma, S.; Beak, P. J. Org. Chem. 2001, 66, 9056. (i) Beal, L. M.; Liu, B.; Chu, W.; Moeller, K. D. Tetrahedron 2000, 56, 10113. (j) Hoffmann, T.; Lanig, H.; Waibel, R.; Gmeiner, P. Angew. Chem. Int. Ed. 2001, 40, 3361. (k) Grossmith, C. E.; Senia, F.; Wagner, J. Synlett 1999, 1660.
- (2003) Tetrahedron , vol.59 , pp. 4501
- Colombo, L.¹ Di Giacomo, M.² Vinci, V.³ Colombo, M.⁴ Manzoni, L.⁵ Scolastico, C.⁶

55
- 0035136833
- For the formation of 7-membered azacycles using RCM see the following: (c) Turling, C. A.; Holmes, A. B.; Markwell, R. E.; Pearson, N. D. J. Chem. Soc., Perkin Trans. 1 1999, 1695. (d) Barrett, A. G. M.; Ahmed, M.; Baker, S. P.; Baugh, S. P. D.; Braddock, D. C.; Procopiou, P. A.; White, A. J. P.; Williams, D. J. J. Org. Chem. 2000, 65, 3716. (e) Martin, S. F.; Chen, H.-J.; Courtney, A. K.; Liao, Y.; Pätzel, M.; Ramser, M. N.; Wagman, A. S. Tetrahedron 1996, 52, 7251. (f) Colombo, L.; Di Giacomo, M.; Vinci, V.; Colombo, M.; Manzoni, L.; Scolastico, C. Tetrahedron 2003, 59, 4501. (g) Vo-Thanh, G.; Boucard, V.; Sauriat-Dorizon, H.; Guibe, F. Synlett 2001, 37. (h) Lim, S. H.; Ma, S.; Beak, P. J. Org. Chem. 2001, 66, 9056. (i) Beal, L. M.; Liu, B.; Chu, W.; Moeller, K. D. Tetrahedron 2000, 56, 10113. (j) Hoffmann, T.; Lanig, H.; Waibel, R.; Gmeiner, P. Angew. Chem. Int. Ed. 2001, 40, 3361. (k) Grossmith, C. E.; Senia, F.; Wagner, J. Synlett 1999, 1660.
- (2001) Synlett , pp. 37
- Vo-Thanh, G.¹ Boucard, V.² Sauriat-Dorizon, H.³ Guibe, F.⁴

56
- 0035966178
- For the formation of 7-membered azacycles using RCM see the following: (c) Turling, C. A.; Holmes, A. B.; Markwell, R. E.; Pearson, N. D. J. Chem. Soc., Perkin Trans. 1 1999, 1695. (d) Barrett, A. G. M.; Ahmed, M.; Baker, S. P.; Baugh, S. P. D.; Braddock, D. C.; Procopiou, P. A.; White, A. J. P.; Williams, D. J. J. Org. Chem. 2000, 65, 3716. (e) Martin, S. F.; Chen, H.-J.; Courtney, A. K.; Liao, Y.; Pätzel, M.; Ramser, M. N.; Wagman, A. S. Tetrahedron 1996, 52, 7251. (f) Colombo, L.; Di Giacomo, M.; Vinci, V.; Colombo, M.; Manzoni, L.; Scolastico, C. Tetrahedron 2003, 59, 4501. (g) Vo-Thanh, G.; Boucard, V.; Sauriat-Dorizon, H.; Guibe, F. Synlett 2001, 37. (h) Lim, S. H.; Ma, S.; Beak, P. J. Org. Chem. 2001, 66, 9056. (i) Beal, L. M.; Liu, B.; Chu, W.; Moeller, K. D. Tetrahedron 2000, 56, 10113. (j) Hoffmann, T.; Lanig, H.; Waibel, R.; Gmeiner, P. Angew. Chem. Int. Ed. 2001, 40, 3361. (k) Grossmith, C. E.; Senia, F.; Wagner, J. Synlett 1999, 1660.
- (2001) J. Org. Chem. , vol.66 , pp. 9056
- Lim, S.H.¹ Ma, S.² Beak, P.³

57
- 0034704303
- For the formation of 7-membered azacycles using RCM see the following: (c) Turling, C. A.; Holmes, A. B.; Markwell, R. E.; Pearson, N. D. J. Chem. Soc., Perkin Trans. 1 1999, 1695. (d) Barrett, A. G. M.; Ahmed, M.; Baker, S. P.; Baugh, S. P. D.; Braddock, D. C.; Procopiou, P. A.; White, A. J. P.; Williams, D. J. J. Org. Chem. 2000, 65, 3716. (e) Martin, S. F.; Chen, H.-J.; Courtney, A. K.; Liao, Y.; Pätzel, M.; Ramser, M. N.; Wagman, A. S. Tetrahedron 1996, 52, 7251. (f) Colombo, L.; Di Giacomo, M.; Vinci, V.; Colombo, M.; Manzoni, L.; Scolastico, C. Tetrahedron 2003, 59, 4501. (g) Vo-Thanh, G.; Boucard, V.; Sauriat-Dorizon, H.; Guibe, F. Synlett 2001, 37. (h) Lim, S. H.; Ma, S.; Beak, P. J. Org. Chem. 2001, 66, 9056. (i) Beal, L. M.; Liu, B.; Chu, W.; Moeller, K. D. Tetrahedron 2000, 56, 10113. (j) Hoffmann, T.; Lanig, H.; Waibel, R.; Gmeiner, P. Angew. Chem. Int. Ed. 2001, 40, 3361. (k) Grossmith, C. E.; Senia, F.; Wagner, J. Synlett 1999, 1660.
- (2000) Tetrahedron , vol.56 , pp. 10113
- Beal, L.M.¹ Liu, B.² Chu, W.³ Moeller, K.D.⁴

58
- 0035903517
- For the formation of 7-membered azacycles using RCM see the following: (c) Turling, C. A.; Holmes, A. B.; Markwell, R. E.; Pearson, N. D. J. Chem. Soc., Perkin Trans. 1 1999, 1695. (d) Barrett, A. G. M.; Ahmed, M.; Baker, S. P.; Baugh, S. P. D.; Braddock, D. C.; Procopiou, P. A.; White, A. J. P.; Williams, D. J. J. Org. Chem. 2000, 65, 3716. (e) Martin, S. F.; Chen, H.-J.; Courtney, A. K.; Liao, Y.; Pätzel, M.; Ramser, M. N.; Wagman, A. S. Tetrahedron 1996, 52, 7251. (f) Colombo, L.; Di Giacomo, M.; Vinci, V.; Colombo, M.; Manzoni, L.; Scolastico, C. Tetrahedron 2003, 59, 4501. (g) Vo-Thanh, G.; Boucard, V.; Sauriat-Dorizon, H.; Guibe, F. Synlett 2001, 37. (h) Lim, S. H.; Ma, S.; Beak, P. J. Org. Chem. 2001, 66, 9056. (i) Beal, L. M.; Liu, B.; Chu, W.; Moeller, K. D. Tetrahedron 2000, 56, 10113. (j) Hoffmann, T.; Lanig, H.; Waibel, R.; Gmeiner, P. Angew. Chem. Int. Ed. 2001, 40, 3361. (k) Grossmith, C. E.; Senia, F.; Wagner, J. Synlett 1999, 1660.
- (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 3361
- Hoffmann, T.¹ Lanig, H.² Waibel, R.³ Gmeiner, P.⁴

59
- 0032826155
- For the formation of 7-membered azacycles using RCM see the following: (c) Turling, C. A.; Holmes, A. B.; Markwell, R. E.; Pearson, N. D. J. Chem. Soc., Perkin Trans. 1 1999, 1695. (d) Barrett, A. G. M.; Ahmed, M.; Baker, S. P.; Baugh, S. P. D.; Braddock, D. C.; Procopiou, P. A.; White, A. J. P.; Williams, D. J. J. Org. Chem. 2000, 65, 3716. (e) Martin, S. F.; Chen, H.-J.; Courtney, A. K.; Liao, Y.; Pätzel, M.; Ramser, M. N.; Wagman, A. S. Tetrahedron 1996, 52, 7251. (f) Colombo, L.; Di Giacomo, M.; Vinci, V.; Colombo, M.; Manzoni, L.; Scolastico, C. Tetrahedron 2003, 59, 4501. (g) Vo-Thanh, G.; Boucard, V.; Sauriat-Dorizon, H.; Guibe, F. Synlett 2001, 37. (h) Lim, S. H.; Ma, S.; Beak, P. J. Org. Chem. 2001, 66, 9056. (i) Beal, L. M.; Liu, B.; Chu, W.; Moeller, K. D. Tetrahedron 2000, 56, 10113. (j) Hoffmann, T.; Lanig, H.; Waibel, R.; Gmeiner, P. Angew. Chem. Int. Ed. 2001, 40, 3361. (k) Grossmith, C. E.; Senia, F.; Wagner, J. Synlett 1999, 1660.
- (1999) Synlett , pp. 1660
- Grossmith, C.E.¹ Senia, F.² Wagner, J.³

60
- 2942723699
- note
- 3Na: 232.0944; found: 232.0940.

61
- 2942747645
- note
- Also see ref. 4c for a similar reduction and establishment of stereocenter at C-9 and C-10.

62
- 2942749528
- note
- Lactone 6 could also be methylated to provide C-9, C-10 diepi stemoamide (data not shown).

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.