Intramolecular Diels-Alder Additions of Benzynes to Furans. Application to the Total Synthesis of Biflorin, and the Mansonone-E, I and F

1986 ◽  
Vol 39 (4) ◽  
pp. 647 ◽  
Author(s):  
WM Best ◽  
D Wege
Keyword(s):  
Total Synthesis ◽  
Anthranilic Acid ◽  
Diels Alder ◽  
Furan Moiety ◽  
Derivatives Of

Benzynes, generated either by the debromination of an appropriately substituted (o-dibromobenzene, or by the thermolysis of a substituted diazotized anthranilic acid, have been trapped intramolecularly by an attached furan moiety. One such adduct (41) has been transformed into 6,9-dimethylnaphtho[1,8-bc]pyran-3(2H)-one (43), which served as the key intermediate for the total synthesis of the title compounds, all of which are derivatives of 6,9-dimethylnaphtho[1,8-bc]pyran-7,8-quinone.

Intramolecular Diels-Alder Additions of Benzynes to Furans. Exploratory Studies

1986 ◽  
Vol 39 (4) ◽  
pp. 635 ◽  
Author(s):  
WM Best ◽  
D Wege
Keyword(s):  
Carboxylic Acid ◽  
Carbon Atom ◽  
Anthranilic Acid ◽  
Furan Ring ◽  
Alkoxy Group ◽  
Diels Alder ◽  
Ring Systems ◽  
Terminal Carbon Atom ◽  
Furan Moiety

A series of 3-alkoxyanthranilic acids, in which a furan ring is attached to the terminal carbon atom of the alkoxy group, has been prepared. When the chain linking the anthranilic acid and furan ring systems is three or four atoms long, decomposition of the derived diazonium chlorides generates the corresponding benzynes , which are efficiently trapped intramolecularly by the furan moiety. Diazotization of 2-amino-3-furfuryloxybenzoic acid, where the linking chain is two atoms long, results in fragmentation with the formation of 6-diazo-5- oxocyclohexa-1,3-diene-1-carboxylic acid.

Catalytic Asymmetric Total Synthesis of (+)- and (−)-Paeoveitol via a Hetero-Diels–Alder Reaction

2017 ◽  
Vol 19 (3) ◽  
pp. 429-431 ◽  
Author(s):  
Tian-Ze Li ◽  
Chang-An Geng ◽  
Xiu-Juan Yin ◽  
Tong-Hua Yang ◽  
Xing-Long Chen ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Asymmetric Total Synthesis ◽  
Diels Alder Reaction ◽  
Catalytic Asymmetric

ChemInform Abstract: SYNTHESES FROM DIMETHYLPYRAZOLES. VII. PYRAZOLE ANALOGS OF ANTHRANILIC ACID AND ITS AMIDE. DERIVATIVES OF N-PYRAZOLYLNAPHTHALIMIDES

1984 ◽  
Vol 15 (37) ◽  
Author(s):  
V. P. PEREVALOV ◽  
M. A. ANDREEVA ◽  
YU. A. MANAEV ◽  
SH. G. ISAEV ◽  
L. I. BARYSHNENKOVA ◽  
...  
Keyword(s):  
Anthranilic Acid ◽  
Amide Derivatives ◽  
Derivatives Of

Simple, efficient total synthesis of cantharidin via a high-pressure Diels-Alder reaction

1980 ◽  
Vol 102 (22) ◽  
pp. 6893-6894 ◽  
Author(s):  
William G. Dauben ◽  
Carl R. Kessel ◽  
Kazuo H. Takemura
Keyword(s):  
High Pressure ◽  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction
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