ChemInform Abstract: The Synthesis of the Monomeric Moiety of Disorazole C1.

ChemInform ◽  
2010 ◽  
Vol 31 (31) ◽  
pp. no-no
Author(s):  
M. C. Hillier ◽  
D. H. Park ◽  
A. T. Price ◽  
R. Ng ◽  
A. I. Meyers
Keyword(s):  
Disorazole C1

The Hoveyda Synthesis of Disorazole C1

2017 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Anticancer Activity ◽  
Vinyl Acetate ◽  
Secondary Alcohol ◽  
Butyl Ester ◽  
Geometric Isomer ◽  
Allylic Alcohol ◽  
Starting Material ◽  
Boston College ◽  
Cross Metathesis ◽  
Disorazole C1

Disorazole C1 3, isolated from fermentation of the myxobacterium Sorangium cellu­losum, shows antifungal and anticancer activity. Amir H. Hoveyda of Boston College applied (J. Am. Chem. Soc. 2014, 136, 16136) recent advances in alkene metathesis from his group to enable the efficient assembly of 2 and so of 3. The ester 1 was assembled from the alcohol 11 and the acid 18. The preparation of 11 began with the enantioselective addition of 5 to 4 to give 6 and then 7, as described by Kalesse (Angew. Chem. Int. Ed. 2010, 49, 1619). Leighton allylation led to 8, that was then coupled with 9 to give 10 with high Z selectivity. Iodination of 10 followed by deprotection then completed the assembly of 11. The starting material for the acid 18 was the allylic alcohol 13. As reported by Cramer (Angew. Chem. Int. Ed. 2008, 47, 6483), exposure of the racemic alcohol 12 to vinyl acetate in the presence of Amano lipase PS converted one enantiomer to the acetate, leaving 13. Methylation of the secondary alcohol followed by acid-mediated removal of the t-butyl ester led to the acid 14, that was converted to the correspond­ing acyl fluoride and coupled with serine Me ester 15 to give 16. After cyclization to the oxazole 17, cross metathesis with five equivalents of 4-bromo-1-butene gave the homoallylic bromide, that was readily eliminated with DBU to give, after saponifica­tion, the acid 18. The cross metathesis of the coupled ester 1, a polyene, with 9 proceeded with remarkable selectivity to give 2, again as the Z geometric isomer. On exposure to the Heck catalyst Pd [(o-tolyl)3P]2, 2 dimerized efficiently. The deprotection was not straightforward, but conditions (H2SiF6, CH3OH, 4°C, 72 h) were found that deliv­ered 3 in 68% yield.

scholarly journals Catalytic Z-Selective Cross-Metathesis in Complex Molecule Synthesis: A Convergent Stereoselective Route to Disorazole C1

2014 ◽  
Vol 136 (46) ◽  
pp. 16136-16139 ◽  
Author(s):  
Alexander W. H. Speed ◽  
Tyler J. Mann ◽  
Robert V. O’Brien ◽  
Richard R. Schrock ◽  
Amir H. Hoveyda
Keyword(s):  
Complex Molecule ◽  
Cross Metathesis ◽  
Disorazole C1

scholarly journals Mitotic slippage in non-cancer cells induced by a microtubule disruptor, disorazole C1

2010 ◽  
Vol 10 (1) ◽  
pp. 1 ◽  
Author(s):  
Fengfeng L Xu ◽  
Youssef Rbaibi ◽  
Kirill Kiselyov ◽  
John S Lazo ◽  
Peter Wipf ◽  
...  
Keyword(s):  
Cancer Cells ◽  
Mitotic Slippage ◽  
Disorazole C1

Total Synthesis of Disorazole C1

Synfacts ◽  
2015 ◽  
Vol 11 (02) ◽  
pp. 0121-0121
Author(s):  
Erick Carreira ◽  
Adrien Joliton
Keyword(s):  
Total Synthesis ◽  
Disorazole C1

scholarly journals Cellular Analysis of Disorazole C1 and Structure-Activity Relationship of Analogs of the Natural Product

2006 ◽  
Vol 67 (1) ◽  
pp. 66-73 ◽  
Author(s):  
Peter Wipf ◽  
Thomas H. Graham ◽  
Andreas Vogt ◽  
Rachel P. Sikorski ◽  
Alexander P. Ducruet ◽  
...  
Keyword(s):  
Natural Product ◽  
Structure Activity Relationship ◽  
Activity Relationship ◽  
Cellular Analysis ◽  
Structure Activity ◽  
Relationship Of ◽  
Disorazole C1

Total Synthesis of (−)-Disorazole C1

2021 ◽  
Author(s):  
Luca Lizzadro ◽  
Oliver Spieß ◽  
Dieter Schinzer
Keyword(s):  
Total Synthesis ◽  
Disorazole C1

Studies on the Total Synthesis of Disorazole C1. An Advanced Macrocycle Intermediate

2001 ◽  
Vol 66 (18) ◽  
pp. 6037-6045 ◽  
Author(s):  
M. C. Hillier ◽  
A. T. Price ◽  
A. I. Meyers
Keyword(s):  
Total Synthesis ◽  
Disorazole C1

scholarly journals Bis-cyclopropane analog of disorazole C1 is a microtubule-destabilizing agent active in abcb1-overexpressing human colon cancer cells

Oncotarget ◽  
2015 ◽  
Vol 6 (38) ◽  
pp. 40866-40879 ◽  
Author(s):  
Shaoyu Wu ◽  
Zhijian Guo ◽  
Chad D. Hopkins ◽  
Ning Wei ◽  
Edward Chu ◽  
...  
Keyword(s):  
Colon Cancer ◽  
Cancer Cells ◽  
Human Colon ◽  
Colon Cancer Cells ◽  
Human Colon Cancer ◽  
Human Colon Cancer Cells ◽  
Disorazole C1

The synthesis of the monomeric moiety of disorazole C1

2000 ◽  
Vol 41 (16) ◽  
pp. 2821-2824 ◽  
Author(s):  
M.C Hillier ◽  
D.H Park ◽  
A.T Price ◽  
R Ng ◽  
A.I Meyers
Keyword(s):  
Disorazole C1

ChemInform Abstract: Catalytic Z-Selective Cross-Metathesis in Complex Molecule Synthesis: A Convergent Stereoselective Route to Disorazole C1.

ChemInform ◽  
2015 ◽  
Vol 46 (21) ◽  
pp. no-no
Author(s):  
Alexander W. H. Speed ◽  
Tyler J. Mann ◽  
Robert V. O'Brien ◽  
Richard R. Schrock ◽  
Amir H. Hoveyda
Keyword(s):  
Complex Molecule ◽  
Cross Metathesis ◽  
Disorazole C1
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