Mechanistic Studies of the Deslongchamps Annulation
The Cs2CO3-mediated annulations ("Deslongchamps annulations") of three spirocyclic benzoquinone monoketals 5b-d with an ester or acyl substituent at C-2 to two tert-butyl esters of λδ-unsaturated β-ketocarboxyl acids ("Nazarov reagents" 2a,b) were monitored 1H NMR spectroscopically. This revealed that a primary product, by all likelihood the Michael adduct, forms fast and prior to the appearance of the Deslongchamps adduct. These primary products form reversibly. This was proved by two crossover and four scavenging experiments. Therein, components already incorporat.
Deslongchamps annulations with benzoquinone monoketals
The so-called Deslongchamps annulation of deprotonated γ, δ-unsaturated β-ketoesters 15 to 2-(alkoxycarbonyl)cyclohex-2-en-1- ones or similarly activated cyclohex-2-en-1-ones offers a versatile access to various kinds of decalindiones. The scope of Deslon
Petrovic, Denis,Brueckner, Reinhard
supporting information; experimental part
p. 6524 - 6527
(2012/02/01)
A route for the enantioselective total synthesis of antheridic acid, the antheridium-inducing factor from anemia phyllitidis
An effective route for the total synthesis of antheridic acid (1) has been devised in which the initial chiral intermediate 7 is generated by enantioselective catalytic reduction and transformed in a stereocontrolled fashion into key intermediates 9, 10, 13, and 2.
Corey,Kigoshi, Hideo
p. 5025 - 5028
(2007/10/02)
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