The intramolecular nitrile oxide cycloaddition (INOC) route to the ergot alkaloids: Use of the isoxazoline to γ-amino alcohol conversion in the total synthesis of (+)-paliclavine

Tetrahedron ◽  
1984 ◽  
Vol 40 (12) ◽  
pp. 2345-2358 ◽  
Author(s):  
Alan P. Kozikowski ◽  
Chen Yon-Yih ◽  
Wang B.C ◽  
Zhang-Bao Xu
Keyword(s):  
Total Synthesis ◽  
Amino Alcohol ◽  
Ergot Alkaloids ◽  
Nitrile Oxide ◽  
Alcohol Conversion

Isolation of ergovaline, ergoptine, and ergonine, new alkaloids of the peptide type, from ergot sclerotia

1979 ◽  
Vol 57 (13) ◽  
pp. 1638-1641 ◽  
Author(s):  
Rudolf Brunner ◽  
Peter Leopold Stütz ◽  
Hans Tscherter ◽  
Paul Albert Stadler
Keyword(s):  
Total Synthesis ◽  
Ergot Alkaloid ◽  
Ergot Alkaloids ◽  
Extraction Processes

The isolation of three new ergot alkaloids of the peptide type from sclerotia of Clavicepspurpurea and from mother liquors of rye ergot alkaloid extraction processes is described. The constitution of the new alkaloids ergovaline, ergoptine, and ergonine has been established by comparison with compounds previously obtained by total synthesis.

ChemInform Abstract: Photocyclization of Enamides. Part 29. Dehydrogenation with Benzeneseleninic Anhydride in the Total Synthesis of Ergot Alkaloids.

ChemInform ◽  
1990 ◽  
Vol 21 (27) ◽  
Author(s):  
I. NINOMIYA ◽  
C. HASHIMOTO ◽  
T. KIGUCHI ◽  
T. NAITO ◽  
D. H. R. BARTON ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Ergot Alkaloids

Total synthesis of the potent antifungal agents bengazole C and E

2009 ◽  
Vol 74 (6) ◽  
pp. 887-900 ◽  
Author(s):  
Álvaro Enríquez-García ◽  
Steven V. Ley
Keyword(s):  
Natural Products ◽  
Antifungal Activity ◽  
Total Synthesis ◽  
Marine Natural Products ◽  
Antifungal Agents ◽  
Nitrile Oxide ◽  
Total Syntheses ◽  
Unique Structure

The bengazoles are marine natural products with unique structure, containing two oxazole rings flanking a single carbon. They show very potent antifungal activity. The total syntheses of bengazole C and E are described following a convergent route which involves diastereoselective cycloaddition of an appropriately substituted nitrile oxide with a butane-1,2-diacetal-protected alkenediol as the key step.

Dehydrogenation with Benzeneseleninic Anhydride in the Total Synthesis of Ergot Alkaloids

1996 ◽  
pp. 529-532
Author(s):  
Ichiya Ninomiya ◽  
Chiyomi Hashimoto ◽  
Toshiko Kiguchi ◽  
Takeaki Naito ◽  
Derek H. R. Barton ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Ergot Alkaloids

Dehydrogenation with phenylseleninic anhydride in the total synthesis of ergot alkaloids

1985 ◽  
Vol 26 (35) ◽  
pp. 4187-4190 ◽  
Author(s):  
Ichiya Ninomiya ◽  
Chiyomi Hashimoto ◽  
Toshiko Kiguchi ◽  
Derek H.R. Barton ◽  
Xavier Lusinchi ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Ergot Alkaloids
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