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Tetrahedron Letters

Volumn 17, Issue 51, 1976, Pages 4701-4704

Useful stereoselective and position-selective transformations of brefeldin A and derivatives at carbons 4, 7 and 15

(2) Corey, E J a Wollenberg, Robert H a

a HARVARD UNIVERSITY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002439662 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(00)93000-4 Document Type: Article

Times cited : (32)

References (25)

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- Cyanein, a new antibiotic fromPenicillium cyaneum
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- J. Antibiotics, Ser. A
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- Betina¹ Drobnica² Nemec³ Zemanová⁴

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- Betina¹

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- Betina¹ Horáková² Baráth³

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- Inhibition of Mitotic Activity in Root Tips of Vicia faba by the Antibiotic Cyanein
- (Tokyo)
- (1964) CYTOLOGIA , vol.29 , pp. 370
- Betina¹ Murin²

8
- 0006466662
- (1964) Naturwiss. , vol.51 , pp. 445
- Baĉiková¹ Betina² Nemec³

9
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- (1968) J. Antibiotics , vol.21 , pp. 160
- Tamura¹ Ando² Suzuki³ Takatsuki⁴ Arima⁵

10
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- (1969) J. Antibiotics , vol.22 , pp. 442
- Takatsuki¹ Yamaguchi² Tamura³ Misato⁴ Arima⁵

11
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- Die Konstitution von Brefeldin A
- (1964) Helvetica Chimica Acta , vol.47 , pp. 1401
- Sigg¹

12
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- The biosynthesis of brefeldin A
- (1969) Australian Journal of Chemistry , vol.22 , pp. 1943
- Coombe¹ Foss² Jacobs³ Watson⁴

13
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- (1971) Helv. Chim. Acta , vol.54 , pp. 2763
- Weber¹ Hauser² Sigg³

14
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- Corey¹ Nicolaou²

15
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- (1975) J. Am. Chem. Soc. , vol.97 , pp. 654
- Corey¹ Nicolaou² Melvin³

16
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- A sample of naturally derived brefeldin A was kindly provided by Dr. H. P. Sigg (Sandoz Ltd., Basle) to whom we are most grateful.

17
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- (1976) Tetrahedron Lett. , pp. 809
- Corey¹ Gras² Ulrich³

18
- 84918026628
- Satisfactory infrared, proton magnetic resonance and mass spectrometric data were obtained for all new compounds described herein.

19
- 84918026627
- It was also observed that the mono-MEM derivative 3 could be obtained selectively in 85% yield from the 4,7-bis-MEM ether of brefeldin under carefully controlled conditions (5 equiv of anhydrous zinc bromide in dry benzene at 40° for 19 hr with rapid stirring).

20
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- (1975) Tetrahedron Lett. , pp. 2647
- Corey¹ Suggs²

21
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- Obviously, mixtures of 3 and the 4β-epimer are convertible to 4.

22
- 84918026625
- 2 at 0°.

23
- 84918026624
- This mixture was not readily separable by chromatography.

24
- 84918026623
- −1.

25
- 84918026622
- This research was assisted financially by a grant from the National Institutes of Health.

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