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Volumn 28, Issue 28, 1987, Pages 3253-3256

Stereoselective synthesis of the middle (C10-C17) and right (C18-C30) segments and their coupling to complete a formal synthesis of the polyether antibiotic salinomycin

(4) Horita, Kiyoshi a Nagato, Satoshi a Oikawa, Yuji a Yonemitsu, Osamu a

a HOKKAIDO UNIVERSITY (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

SALINOMYCIN;

DRUG STRUCTURE; DRUG SYNTHESIS; METHODOLOGY; PRELIMINARY COMMUNICATION;

EID: 0023250839 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(00)95485-6 Document Type: Article

Times cited : (38)

References (33)

1
- 0022528796
- (1986) Tetrahedron Lett. , vol.27 , pp. 3647
- Oikawa¹ Tanaka² Yonemitsu³

2
- 0022493303
- (1986) J. Am. Chem. Soc. , vol.108 , pp. 4645
- Nakajima¹ Hamada² Tanaka³ Oikawa⁴ Yonemitsu⁵

3
- 0000244323
- (1986) Tetrahedron Lett. , vol.27 , pp. 3651
- Tanaka¹ Oikawa² Hamada³ Yonemitsu⁴

4
- 84914285313
- Salinomycin (1), isolated from Streptomyces albus, is a very important anticoccidial agent in the poultry industry and a marvelous total synthesis was achieved by Kishi.

5
- 0016262114
- (1974) J. Antibiot. , vol.27 , pp. 814
- Miyazaki¹ Shibuya² Sugawara³ Kawaguchi⁴ Hirose⁵ Nagatsu⁶ Esumi⁷

6
- 0342288919
- K.J Laidler, Pergamon Press, Oxford
- (1982) Front. Chem. Plenary Keynote Lect. IUPAC Congr. 28th, 1981 , pp. 287-304
- Kishi¹ Hatakeyama² Lewis³

7
- 84914285312
- Unless otherwise noted, the numbering is based on that of salinomycin (1).

8
- 84914285311
- The C10–C30 segment (4) is a retro-aldol and isomerization product of the 20-O-acetyl-1-ester derivative of 1 as well as a key intermediate in Kishi's synthesis.

9
- 84981833185
- Stoffwechselprodukte von Actinomyceten. 5. Mitteilung. �ber das Lacton der ?-Hydroxy-?, ??, ?-trimethyl-pimelins�ure, ein Abbauprodukt von Narbomycin, Pikromycin und Methymycin
- (1956) Helvetica Chimica Acta , vol.39 , pp. 1785
- Anliker¹ Dvornik² Gubler³ Heusser⁴ Prelog⁵

10
- 0000545414
- (1956) J. Am. Chem. Soc. , vol.78 , pp. 2907
- Djerassi¹ Zderic²

11
- 0001409817
- (1956) J. Am. Chem. Soc. , vol.78 , pp. 6390
- Djerassi¹ Zderic²

12
- 84914285310
- (1987) Chem. Pharm. Bull. , vol.35 , pp. 0000
- Oikawa¹ Tanaka² Horita³ Noda⁴ Nakajima⁵ Kakusawa⁶ Hamada⁷ Yonemitsu⁸

13
- 84914285309
- 3 gave 9 with 57 : I stereoselection.

14
- 84914285308
- b.

15
- 84914285307
- A synthetic equivalent of 3 was also synthesized from a C21–C30 segment, an alkaline degradation product of 1, and will be reported soon.

16
- 84914285306
- Since in Kishi's total synthesis of 1 introduction of the C20 chiral center was in uncontrol of stereochemistry, the desired product with the correct C20 configuration was minor and the undesired product was converted to the desired one after repeated recycles, though its efficiency was not so good.

17
- 0021956593
- (1985) Tetrahedron Lett. , vol.26 , pp. 1541
- Oikawa¹ Horita² Yonemitsu³

18
- 0013599288
- (1977) Tetrahedron Lett. , pp. 2417
- Seto¹ Miyazaki² Fujita³ Otake⁴

19
- 0000632111
- (1984) Tetrahedron Lett. , vol.25 , pp. 5397
- Oikawa¹ Tanaka² Horita³ Yonemitsu⁴

20
- 46149140781
- (1986) Tetrahedron , vol.42 , pp. 3021
- Horita¹ Yoshioka² Tanaka³ Oikawa⁴ Yonemitsu⁵

21
- 0000192963
- (1982) Tetrahedron Lett. , vol.23 , pp. 885
- Oikawa¹ Yoshioka² Yonemitsu³

22
- 0000455168
- (1980) Tetrahedron Lett. , vol.21 , pp. 1031
- Still¹ McDonald²

23
- 0000546839
- (1980) Tetrahedron Lett. , vol.21 , pp. 1035
- Still¹ Schneider²

24
- 84914285305
- 2 in the usual way, but a side reaction forming a tetrahydrofuran derivative was unavoidable.

25
- 0010630577
- (1982) J. Am. Chem. Soc. , vol.104 , pp. 6468
- Reed¹ Ito² Masamune³ Sharpless⁴

26
- 84914285304
- 2CuLi at −93°C.

27
- 84914285303
- This compound was almost 1 : 1 mixture with respect to the C21 acetal position.

28
- 33748986528
- (1965) J. Organomet. Chem. , vol.3 , pp. 337
- Seyferth¹ Simmons² Singh³

29
- 0000387501
- (1966) J. Organomet. Chem. , vol.5 , pp. 267
- Seyferth¹ Heeren² Singh³ Grim⁴ Hughes⁵

30
- 84914285302
- 28a, 28b, 28c and 28d were isolated in the ratio of 3.8 : 3.2 : 1.4 : 1.0. Configurations at the bisketal positions were variable in the presence of a trace of acid.

31
- 84914285301
- 28c occurred.

32
- 0017411484
- (1977) J. Antibiot. , vol.30 , pp. 610
- Westly¹ Blount² Evans³ Liu⁴

33
- 84914285300
- The left (C1–C10) segment has been synthesized from D-glucose in this laboratory and will be reported soon.

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