Studies towards the total synthesis of ouabagenin

2005 ◽  
Vol 83 (6-7) ◽  
pp. 728-740 ◽  
Author(s):  
Ling Chen ◽  
Pierre Deslongchamps
Keyword(s):  
Organic Chemistry ◽  
Natural Products ◽  
Total Synthesis ◽  
Michael Reaction ◽  
Alder Reaction ◽  
Diels Alder ◽  
Convergent Synthesis ◽  
Diels Alder Reaction

An anionic cyclization strategy developed in our laboratory was used to produce a versatile and convergent synthesis of an advanced tetracyclic intermediate for the construction of ouabagenin and closely related analogs.Key words: organic chemistry, synthesis, cycloaddition, polycyclization, Michael reaction, Diels–Alder reaction, steroids, oubain, ouabagenin, natural products.

Recent applications of the hetero Diels–Alder reaction in the total synthesis of natural products

RSC Advances ◽  
2015 ◽  
Vol 5 (123) ◽  
pp. 101999-102075 ◽  
Author(s):  
Majid M. Heravi ◽  
Tahereh Ahmadi ◽  
Mahdieh Ghavidel ◽  
Bahareh Heidari ◽  
Hoda Hamidi
Keyword(s):  
Organic Chemistry ◽  
Natural Products ◽  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Synthetic Utility

The synthetic utility and potential power of the Diels–Alder (D–A) reaction in organic chemistry is evident.

ChemInform Abstract: Recent Applications of the Hetero Diels-Alder Reaction in the Total Synthesis of Natural Products

ChemInform ◽  
2016 ◽  
Vol 47 (9) ◽  
pp. no-no
Author(s):  
Majid M. Heravi ◽  
Tahereh Ahmadi ◽  
Mahdieh Ghavidel ◽  
Bahareh Heidari ◽  
Hoda Hamidi
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

The intramolecular Diels–Alder reaction: recent advances and synthetic applications

1984 ◽  
Vol 62 (2) ◽  
pp. 183-234 ◽  
Author(s):  
Alex G. Fallis
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Synthetic Strategy ◽  
Diels Alder Reaction ◽  
Recent Advances ◽  
Cyclic Dienes

Recent advances and examples of the intramolecular Diels–Alder reaction are summarized and applications to the total synthesis of natural products, both completed and in progress, noted. A detailed discussion of trienes leading to bicyclo[4.3.0]nonene skeletons is followed by examples of bicyclo[4.4.0]decenes and adducts arising from ortho-quinodimethane precursors. Cycloadditions affording bicyclo[n.4.0] systems and bridged-ring adducts from cyclic dienes conclude this survey which is followed by a discussion of unreactive trienes and a brief analysis of synthetic strategy to complete the review.

scholarly journals Thiourea-catalyzed Diels–Alder reaction of a naphthoquinone monoketal dienophile

2013 ◽  
Vol 9 ◽  
pp. 1414-1418 ◽  
Author(s):  
Carsten S Kramer ◽  
Stefan Bräse
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Selective Synthesis ◽  
Quaternary Center ◽  
Diels Alder Reaction ◽  
Cycloaddition Product ◽  
Sterically Hindered ◽  
First Time

A variety of organocatalysts were screened for the catalysis of the naphthoquinone monoketal Diels–Alder reaction. In this study we found that Schreiner's thiourea catalyst 10 and Jacobson's thiourea catalyst 12 facilitate the cycloaddition of the sterically hindered naphthoquinone monoketal dienophile 3 with diene 4. The use of thiourea catalysis allowed for the first time the highly selective synthesis of the exo-product 2a in up to 63% yield. In this reaction a new quaternary center was built. The so formed cycloaddition product 2a represents the ABC tricycle of beticolin 0 (1) and is also a valuable model substrate for the total synthesis of related natural products.

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