The total synthesis of (±)-petasitolone

1984 ◽  
Vol 62 (12) ◽  
pp. 2676-2681 ◽  
Author(s):  
Hsing-Jang Liu ◽  
Teng Ko Ngooi
Keyword(s):  
Total Synthesis ◽  
Lewis Acid ◽  
Good Yield ◽  
Ring System ◽  
Diels Alder ◽  
Efficient Synthesis ◽  
Target Molecule ◽  
Rapid Construction ◽  
Excellent Control ◽  
Acid Catalyzed

The total synthesis of petasitolone (1), a sesquiterpenoid of the eremophilane family, has been accomplished. The key step of this efficient synthesis is the Lewis acid catalyzed Diels–Alder addition of 2-carbomethoxy-2-cyclohexenone (3) to diene 9. The cycloaddition, which gives adduct 16 in good yield, facilitates the rapid construction of the parent ring system of the target molecule and allows an excellent control of the required stereochemistry.

An approach towards the construction of the tetracyclic skeleton of palhinine alkaloids

2020 ◽  
Vol 7 (16) ◽  
pp. 2243-2246 ◽  
Author(s):  
Congcong Han ◽  
Yang Chen ◽  
Yin-Cheung Ching ◽  
Chi-Sing Lee ◽  
Shuzhong He
Keyword(s):  
Lewis Acid ◽  
Diels Alder ◽  
Cascade Process ◽  
Rapid Construction ◽  
Acid Catalyzed ◽  
Tetracyclic Core

A bifunctional Lewis acid catalyzed Diels–Alder/carbocyclization cascade process was developed for the rapid construction of the tetracyclic core of palhinine alkaloids.

Lewis acid catalyzed diels-alder reactions of S-(+)-carvone1 with silyloxy dienes. Total synthesis of (+)-α-cyperone.

Tetrahedron ◽  
1992 ◽  
Vol 48 (15) ◽  
pp. 3121-3130 ◽  
Author(s):  
Anja A. Haaksma ◽  
Ben J.M. Jansen ◽  
Aede de Groot
Keyword(s):  
Total Synthesis ◽  
Lewis Acid ◽  
Diels Alder ◽  
Acid Catalyzed

scholarly journals Activated cyclooctenones are effective dienophiles

1997 ◽  
Vol 75 (6) ◽  
pp. 899-912 ◽  
Author(s):  
Hsing-Jang Liu ◽  
Dan-Xiong Wang ◽  
Jeung Bea Kim ◽  
Eric N.C. Browne ◽  
Yu Wang
Keyword(s):  
Lewis Acid ◽  
Alder Reaction ◽  
Ring System ◽  
Diels Alder ◽  
Substitution Pattern ◽  
Diels Alder Reaction ◽  
Factors Influencing ◽  
Fused Ring ◽  
Acid Catalyzed ◽  
Fused Ring System

The first Diels–Alder addition of a diene to a cyclooctenone dienophile has been observed. Three activated cyclooctenone dienophiles 1, 2, and 3 are studied with a variety of simple and functionalized dienes. Diels–Alder adducts are produced in excellent yields under very mild Lewis acid catalyzed conditions. The usual orientation rules are followed and, as predicted, the products are formed for the most part exclusively by ester-endo addition. The stereoselectivity is influenced by the substitution pattern of the diene in some cases. The factors influencing the stereochemical selectivity of the addition are discussed in some detail. Keywords: 2-carbalkoxy-2-cyclooctenones, Diels–Alder reaction, six–eight fused ring system.

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