Microwave-assisted Diels–Alder reaction of 1,3,3-trimethyl-2-vinyl-1-cyclohexene with chromones — An expeditious approach to analogues of the puupehenone group of marine diterpenoids and kampanols

2010 ◽  
Vol 88 (12) ◽  
pp. 1233-1239 ◽  
Author(s):  
Rajesh M. Kamble ◽  
M. M.V. Ramana

A rapid assembly of the tetracyclic core of marine diterpenoids related to puupehenone and kampanols by a Diels–Alder reaction of 1,3,3-trimethyl-2-vinyl-1-cyclohexene with chromones under microwave irradiation with or without TiCl4 is described.

ChemInform ◽  
2010 ◽  
Vol 27 (38) ◽  
pp. no-no
Author(s):  
B. GARRIGUES ◽  
C. LAPORTE ◽  
R. LAURENT ◽  
A. LAPORTERIE ◽  
J. DUBAC

Synlett ◽  
2008 ◽  
Vol 2008 (18) ◽  
pp. 2877-2881 ◽  
Author(s):  
Yoshihisa Kobayashi ◽  
Stephen Born ◽  
Genesis Bacani ◽  
Erin Olson

2001 ◽  
Vol 79 (12) ◽  
pp. 1906-1909 ◽  
Author(s):  
Christopher K Jankowski ◽  
Gaëtan LeClair ◽  
Jacqueline MR Bélanger ◽  
Jocelyn RJ Paré ◽  
Marie-Rose VanCalsteren

The synthesis of isoquinolinone carboxylates was performed using arecoline or its isomer N-methyl tetrahydro pyridine carboxylate with Danishefsky's diene via thermal or microwave assisted Diels-Alder reaction. The comparison of both condensation modes showed that the microwave method not only afforded higher yields of the adducts, but also lead to the formation of a new α,β-unsaturated pyridyl ketone. All structures were identified with the help of high resolution 2D NMR.Key words: Diels-Alder microwave assisted reaction, microwave synthesis, Michael, diene, isoquinoline carboxylate synthesis, Danishefsky diene synthesis, MAP Diels-Alder2.


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