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Journal of Labelled Compounds and Radiopharmaceuticals

Volumn 51, Issue 5, 2008, Pages 218-225

Efficient syntheses of 13C-labelled erythromycin biosynthetic intermediates. 2: (2S,3S,4S,5R,6R,7R)-3,6,7-trihydroxy-2,4,6-trimethyl[1- 13C]nonan-5-olide and S-2-acetylaminoethyl (2R,3S,4S,5R,6S,7R)-3,5,6, 7-tetrahydroxy-2,4,6-trimethyl [1-13C]nonanethioate

(5) Iida, Katsumi b Kajiwara, Masahiro b Fukui, Mineo c Nakata, Tadashi a,c Oishi, Takeshi c

a TOKYO UNIVERSITY OF SCIENCE (Japan)

b MEIJI PHARMACEUTICAL UNIVERSITY (Japan)

c INST OF PHYS AND CHEMICAL RESEARCH (Japan)

Author keywords

13C labelling synthesis; Erythromycin biosynthetic intermediate; Sodium 1 13C propionate

Indexed keywords

ANTIBIOTICS; BIOCHEMISTRY; BIOSYNTHESIS; CONDENSATION REACTIONS; KETONES;

13-C LABELING; 13C-LABELING SYNTHESIS; ALDOL CONDENSATION; CHAIN ELONGATION; EFFICIENT SYNTHESIS; ERYTHROMYCIN BIOSYNTHESIS; ERYTHROMYCIN BIOSYNTHETIC INTERMEDIATE; SODIUM [1-13C]PROPIONATE; SYNTHESISED; TRIMETHYL;

SODIUM;

3,6,7 TRIHYDROXY 2,4,6 TRIMETHYL 1 NONAN 5 OLIDE C 11; ACETYLAMINOETHYL 3,5,6,7 TETRAHYDROXY 2,4,6 TRIMETHYL 1 NONANETHIOATE C 11; ALDEHYDE DERIVATIVE; ERYTHROMYCIN; ERYTHROMYCIN DERIVATIVE; RADIOLIGAND; SODIUM DERIVATIVE;

ALDOL REACTION; ARTICLE; CHEMICAL STRUCTURE; DRUG SYNTHESIS; ISOTOPE LABELING; STRUCTURE ANALYSIS;

EID: 46949105999 PISSN: 03624803 EISSN: 10991344 Source Type: Journal
DOI: 10.1002/jlcr.1506 Document Type: Article

Times cited : (1)

References (26)

1
- 0019839727
- D. E. Cane, H. Hasler, T.-C. Liang, J. Am. Chem. Soc. 1981, 103, 5960-5962.
- (1981) J. Am. Chem. Soc , vol.103 , pp. 5960-5962
- Cane, D.E.¹ Hasler, H.² Liang, T.-C.³

2
- 0021052357
- D. E. Cane, H. Hasler, P. B. Taylor, T.-C. Liang, Tetrahedron 1983, 39, 3449-3455.
- (1983) Tetrahedron , vol.39 , pp. 3449-3455
- Cane, D.E.¹ Hasler, H.² Taylor, P.B.³ Liang, T.-C.⁴

3
- 0022548531
- D. E. Cane, T.-C. Liang, P. B. Taylor, C. Chang, C.-C. Yang, J. Am. Chem. Soc. 1986, 108, 4957-4964.
- (1986) J. Am. Chem. Soc , vol.108 , pp. 4957-4964
- Cane, D.E.¹ Liang, T.-C.² Taylor, P.B.³ Chang, C.⁴ Yang, C.-C.⁵

4
- 0023098840
- D. E. Cane, C.-C. Yang, J. Am. Chem. Soc. 1987, 109, 1255-1257.
- (1987) J. Am. Chem. Soc , vol.109 , pp. 1255-1257
- Cane, D.E.¹ Yang, C.-C.²

5
- 0025936258
- D. E. Cane, P. C. Prabhakaran, W. Tan, W. R. Ott, Tetrahedron Lett. 1991, 32, 5457-5460.
- (1991) Tetrahedron Lett , vol.32 , pp. 5457-5460
- Cane, D.E.¹ Prabhakaran, P.C.² Tan, W.³ Ott, W.R.⁴

6
- 0025081416
- DOI: 10.1038/348176a0
- J. Cortes, S. F. Haydock, G. A. Roberts, D. J. Bevitt, P. F. Leadlay, Nature 1990, 348, 176-178. DOI: 10.1038/348176a0.
- (1990) Nature , vol.348 , pp. 176-178
- Cortes, J.¹ Haydock, S.F.² Roberts, G.A.³ Bevitt, D.J.⁴ Leadlay, P.F.⁵

7
- 0025335890
- J. S. Tuan, J. M. Weber, M. J. Staver, J. O. Leung, S. Donadio, L. Katz, Gene 1990, 90, 21-29.
- (1990) Gene , vol.90 , pp. 21-29
- Tuan, J.S.¹ Weber, J.M.² Staver, M.J.³ Leung, J.O.⁴ Donadio, S.⁵ Katz, L.⁶

8
- 0026511543
- D. J. Bevitt, J. Cortes, S. F. Haydock, P. F. Leadlay, Eur. J. Biochem. 1992, 204, 39-49.
- (1992) Eur. J. Biochem , vol.204 , pp. 39-49
- Bevitt, D.J.¹ Cortes, J.² Haydock, S.F.³ Leadlay, P.F.⁴

9
- 0026415106
- S. Donadio, M. J. Staver, J. B. McAlpine, S. J. Swanson, L. Katz, Science 1991, 252, 675-679.
- (1991) Science , vol.252 , pp. 675-679
- Donadio, S.¹ Staver, M.J.² McAlpine, J.B.³ Swanson, S.J.⁴ Katz, L.⁵

10
- 85167473163
- See the accompanying paper
- See the accompanying paper.

11
- 0003661444
- Total synthesis of macrolides
- Ed, S. Omura, Academic Press, New York
- S. Masamune, P. A. McCarthy, Total synthesis of macrolides. In Macrolide Antibiotics-Chemistry, Biology, and Practice, Chapter 4 (Ed.: S. Omura), Academic Press, New York, 1984, pp. 127-198.
- (1984) Macrolide Antibiotics-Chemistry, Biology, and Practice , pp. 127-198
- Masamune, S.¹ McCarthy, P.A.²

12
- 0023891875
- T. Nakata, M. Fukui, T. Oishi, Tetrahedron Lett. 1988, 29, 2219-2222.
- (1988) Tetrahedron Lett , vol.29 , pp. 2219-2222
- Nakata, T.¹ Fukui, M.² Oishi, T.³

13
- 0023951228
- T. Nakata, M. Fukui, T. Oishi, Tetrahedron Lett. 1988, 29, 2223-2226.
- (1988) Tetrahedron Lett , vol.29 , pp. 2223-2226
- Nakata, T.¹ Fukui, M.² Oishi, T.³

14
- 85167478505
- The experiments shown in Scheme 2 are described in the supplemental data.
- The experiments shown in Scheme 2 are described in the supplemental data.

15
- 0001924336
- Eds, N. L. Allinger, E. L. Eliel, S. H. Wilen, Wiley, New York
- D. A. Evans, J. V. Nelson, T. R. Taber, In Topics in Stereochemistry, Vol. 13 (Eds.: N. L. Allinger, E. L. Eliel, S. H. Wilen), Wiley, New York, 1982, pp. 1-115.
- (1982) Topics in Stereochemistry , vol.13 , pp. 1-115
- Evans, D.A.¹ Nelson, J.V.² Taber, T.R.³

16
- 85167471131
- C. H. Heathcock, Comprehensive Carbanion Chemistry. In Studies in Organic Chemistry, 5, Part B, Chapter 4 (Eds.: E. Buncel, T. Durst), Elsevier, Amsterdam, 1984, pp. 177-237.
- C. H. Heathcock, Comprehensive Carbanion Chemistry. In Studies in Organic Chemistry, Vol. 5, Part B, Chapter 4 (Eds.: E. Buncel, T. Durst), Elsevier, Amsterdam, 1984, pp. 177-237.

17
- 0000584420
- Ed, J. D. Morrison, Academic Press, New York
- C. H. Heathcock, In Asymmetric Synthesis, Vol. 3 (Ed.: J. D. Morrison), Academic Press, New York, 1984, pp. 111-212.
- (1984) Asymmetric Synthesis , vol.3 , pp. 111-212
- Heathcock, C.H.¹

18
- 0001160781
- M. C. Pirrung, C. H. Heathcock, J. Org. Chem. 1980, 45, 1727-1728.
- (1980) J. Org. Chem , vol.45 , pp. 1727-1728
- Pirrung, M.C.¹ Heathcock, C.H.²

19
- 85167472556
- 1H NMR (CDCl3) data of 8a; δ: 0.14 (s, 9H, Si(CHcombining low line3)3, 0.15 (s, 9H, Si(CHcombining low line3)3, 0.17 (s, 9H, Si(CHcombining low line3)3, 0.91 (d, 3H, J, 7.1 Hz, 4-CHcombining low line3, 0.92 (t, 3H, J, 7.6 Hz, 9-Hcombining low line3, 1.23 (s, 3H, 6-CHcombining low line 3, 1.31 (d, 3H, J, 7.1 Hz, 2-CHcombining low line 3, 1.44 (m, 1H, 8-Hcombining low line, 1.56 (m, 1H, 8-Hcombining low line, 2.07 (m, 1H, 4-Hcombining low line, 2.18 (s, 6H, Ph(CHcombining low line3)2, 2.66 (d, 1H, J, 10.3 Hz, 3-OHcombining low line, 2.85 (dq, 1H, J, 7.1, 9.5 Hz, 2-Hcombining low line, 3.49 (dd, 1H, J, 2.2, 9.5 Hz, 7-Hcombining low line, 3.80 (d, 1H, J, 3.2 Hz, 5-Hcombining low line, 3.93 (d, 1H, J, 10.0 Hz, 3-Hcombining low line, 7.04 s, 3H, ph
- 3).

20
- 85167474815
- 3), 1.40 (m, 1H, 8-Hcombining low line), 1.72 (m, 1H, 8-Hcombining low line), 2.22 (m, 1H, 4-Hcombining low line), 2.72 (dt, 1H, J = 3.7, 7.6 Hz, 2-Hcombining low line), 3.40 (dt, 1H, J = 1.8, 11.0 Hz, 7-Hcombining low line), 3.88 (dt, 1H, J = 3.7, 11.9 Hz, 3-Hcombining low line), 4.97 (d, 1H, J = 2.8 Hz, 5-Hcombining low line).
- 3), 1.40 (m, 1H, 8-Hcombining low line), 1.72 (m, 1H, 8-Hcombining low line), 2.22 (m, 1H, 4-Hcombining low line), 2.72 (dt, 1H, J = 3.7, 7.6 Hz, 2-Hcombining low line), 3.40 (dt, 1H, J = 1.8, 11.0 Hz, 7-Hcombining low line), 3.88 (dt, 1H, J = 3.7, 11.9 Hz, 3-Hcombining low line), 4.97 (d, 1H, J = 2.8 Hz, 5-Hcombining low line).

21
- 0012016624
- D. A. Evans, J. Bartroli, T. L. Shih, J. Am. Chem. Soc. 1981, 103, 2127-2129.
- (1981) J. Am. Chem. Soc , vol.103 , pp. 2127-2129
- Evans, D.A.¹ Bartroli, J.² Shih, T.L.³

22
- 0004698036
- F. J. Leeper, S. E. Shaw, P. Satish, Can. J. Chem. 1994, 72, 131-141.
- (1994) Can. J. Chem , vol.72 , pp. 131-141
- Leeper, F.J.¹ Shaw, S.E.² Satish, P.³

23
- 37049093198
- J. Herscovici, K. Antonakis, Chem. Comm. 1980, 561-562.
- (1980) Chem. Comm , pp. 561-562
- Herscovici, J.¹ Antonakis, K.²

24
- 84988107382
- S. L. Huang, K. Omura, D. Swern, Synthesis 1978, 297-298.
- (1978) Synthesis , pp. 297-298
- Huang, S.L.¹ Omura, K.² Swern, D.³

25
- 0000173342
- N. Nakata, T. Oishi, Tetrahedron Lett. 1980, 21, 1641-1644.
- (1980) Tetrahedron Lett , vol.21 , pp. 1641-1644
- Nakata, N.¹ Oishi, T.²

26
- 0001576379
- S. Yamada, Y. Yokoyama, T. Shioiri, J. Org. Chem. 1974, 39, 3302-3303.
- (1974) J. Org. Chem , vol.39 , pp. 3302-3303
- Yamada, S.¹ Yokoyama, Y.² Shioiri, T.³

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