Total synthesis of d,l-coronafacic acid by an intermolecular Diels–Alder approach

1984 ◽  
Vol 62 (9) ◽  
pp. 1747-1750 ◽  
Author(s):  
Hsing-Jang Liu ◽  
Montse Llinas-Brunet
Keyword(s):  
Total Synthesis ◽  
Diels Alder ◽  
Keto Ester ◽  
Coronafacic Acid

An efficient total synthesis of d,l-coronafacic acid (2) has been achieved from 4-cyclopentene-1,3-dione (4). The synthesis involves keto ester 7 as a key intermediate that is conveniently prepared by the Diels–Alder addition of enedione 4 to ethyl 4-ethyl-2,4-pentadienoate (5).

Total synthesis of androstanes

1979 ◽  
Vol 57 (24) ◽  
pp. 3356-3358 ◽  
Author(s):  
Masatoshi Kakushima ◽  
Jagabandhu Das ◽  
Gary R. Reid ◽  
Peter S. White ◽  
Zdenek Valenta
Keyword(s):  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Keto Ester ◽  
Diels Alder Reaction ◽  
Androstane Derivatives

A total synthesis of androstane derivatives is described. The desired configuration at C8 and at C13 is achieved in a ring C forming SnCl4-catalyzed Diels–Alder reaction. The preparation of methyl Z-2-methyl-4-oxo-2-pentenoate and the cyclization of a keto ester to a steroid 15,17-dione are also reported.

Total synthesis of amphilectane-type diterpenoids: (±)-8,15-diisocyano-11(20)-amphilectene

1993 ◽  
Vol 71 (9) ◽  
pp. 1484-1494 ◽  
Author(s):  
Edward Piers ◽  
Montse Llinas-Brunet ◽  
Renata M. Oballa
Keyword(s):  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Allylic Oxidation ◽  
Keto Ester ◽  
Efficient Transformation ◽  
Diels Alder Reaction ◽  
Product Mixture

A total synthesis of the structurally novel, antimicrobial diterpenoid (±)-8,15-diisocyano-11(20)-amphilectene (2) is described. Alkylation of 2-methoxycarbonyl-3-methylcyclohexanone (13) with (E)-1-(tert-butyldimethylsiloxy)-6-iodo-3-(trimethylstannyl)-2-hexene (14) provided, stereoselectively, the functionalized keto ester 15, which was converted efficiently into the diene 17. Diels–Alder reaction of 17 with acrolein, followed by base-catalyzed equilibration of the resultant product mixture, gave the aldehydes 19 (58%) and 20 (29%). Allylic oxidation of the alkene 24 (derived from 19) afforded the enone 25. Reduction (Na, NH3, t-BuOH) of 25 gave 28, which was converted, via a sequence of eight synthetic steps, into the diacid 45. Efficient transformation of the carboxyl functions of 45 into isonitrile groups completed the synthesis of (±)-2.

Total synthesis of α- and β-himachalene by an intermolecular Diels–Alder approach

1981 ◽  
Vol 59 (3) ◽  
pp. 601-608 ◽  
Author(s):  
Hsing-Jang Liu ◽  
Eric N. C. Browne
Keyword(s):  
Total Synthesis ◽  
Diels Alder ◽  
Keto Ester

A total synthesis of α-himachalene (2) and β-himachalene (3) has been achieved in eleven steps and in an effective overall yield of 21% from 4,4-dimethyl-2-cyclohexenone (4). The synthesis involves keto ester 7 as a key intermediate which is conveniently prepared by the Diels–Alder addition of dienone ester 6 to isoprene.

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
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