ChemInform Abstract: On the Reactivity of N,N-Bis(trimethyl)silylated Enamines: Model Studies on Hetero Diels-Alder Reactions and Other Cycloadditions.

ChemInform ◽  
2010 ◽  
Vol 26 (34) ◽  
pp. no-no
Author(s):  
K. PAULINI ◽  
H.-U. REISSIG ◽  
P. RADEMACHER
Keyword(s):  
Diels Alder ◽  
Model Studies

Model studies on construction of the oxabicyclic [3.3.1] core of the mulberry Diels–Alder adducts morusalbanol A and 441772-64-1

2015 ◽  
Vol 56 (36) ◽  
pp. 5082-5085 ◽  
Author(s):  
Jia Ti Tee ◽  
Chin Fei Chee ◽  
Michael J.C. Buckle ◽  
Vannajan Sanghiran Lee ◽  
Wei Lim Chong ◽  
...  
Keyword(s):  
Diels Alder ◽  
Model Studies

ChemInform Abstract: Intramolecular Diels-Alder Reactions of Cyclopentadiene Systems: Model Studies for the Total Synthesis of the Capnellenes.

ChemInform ◽  
1988 ◽  
Vol 19 (35) ◽  
Author(s):  
J. HELLOU ◽  
G. BERUBE ◽  
M. J. NEWLANDS ◽  
A. G. FALLIS ◽  
E. J. GABE
Keyword(s):  
Total Synthesis ◽  
Diels Alder ◽  
Model Studies ◽  
Systems Model

Asymmetric synthesis of podophyllotoxin analogs

1990 ◽  
Vol 68 (11) ◽  
pp. 2022-2027 ◽  
Author(s):  
James L. Charlton ◽  
Guy L. Plourde ◽  
K. Koh ◽  
Anthony S. Secco
Keyword(s):  
Asymmetric Synthesis ◽  
Natural Product ◽  
Good Yield ◽  
Diels Alder ◽  
Cycloaddition Reactions ◽  
Thermal Generation ◽  
Methyl Lactate ◽  
Model Studies ◽  
Diastereomeric Excess ◽  
Absolute Stereochemistry

Two analogs of podophyllotoxin, with the same absolute stereochemistry as the natural product, have been synthesized from the cycloadduct between α-hydroxy-α′-phenyl-o-quinodimefhane and the fumarate of S-methyl lactate. After initial attempts to produce the cycloadduct from photochemically generated α-hydroxy-α′-phenyl-o-quinodimethane failed, a study of the thermal generation and reaction of α-hydroxy-o-quinodimethane with the fumarate and acrylate of S-methyl lactate was made. A comparison was made of the diastereoselectivity of these cycloaddition reactions to those previously reported, in which the o-quinodimethane was generated photochemically. The α-hydroxy-o-quinodimethane was produced both by the known thermolysis of benzocyclobutenol and by thermolysis of 1-hydroxy-1,3-dihydrobenzo[c]thiophene-2,2-dioxide. The diastereomeric excess for the cycloaddition reactions was found to be greater than 95% with modest (ca. 55%) isolated yields of the major cycloadducts. Following these model studies, it was found that α-hydroxy-α′-phenyl-o-quinodimethane produced thermally from 1-hydroxy-3-phenyl-1,3-dihydrobenzo[c]thiophene-2,2-dioxide could be added to the fumarate of S-methyl lactate with high diastereoselectivity and good yield. The product of this reaction was converted to the podophyllotoxin analogs 7 and 17. Keywords: o-quinodimethanes, asymmetric, Diels–Alder, lactate, podophyllotoxin, lignan.

Silicon-substituted dienes in the intramolecular Diels-Alder reaction: nagilactone model studies

1983 ◽  
Vol 48 (4) ◽  
pp. 454-459 ◽  
Author(s):  
Steven D. Burke ◽  
Sharon M. Smith Strickland ◽  
Tory H. Powner
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Model Studies ◽  
Diels Alder Reaction
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