lutesium (Newbee)
08-26-04 22:01
No 527553
      Ent. Selective Syntheses of Subst. Butyrolactones     

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Enantioselective Syntheses of Substituted ƒ×ƒ{ -Butyrolactones
 

Ernest L. Eliel, Xu Bai and Masaki Ohwa
 
 
Abstract.     The previously described chiral 2-acyloxathianes 5(Scheme I) are used in two different enantioselective syntheses of g-butyrolactones. In one synthesis, Grignard addition, cleavage and reduction to carbinols RR'C(OH)CH2OH is followed by tosylation, malonate homologation, lactonization, and removal of the carbomethoxy group to give optically active g-lactones. A modification of this synthesis (Scheme I) leads to optically active a-methylene-g-lactones. In the second synthesis, reaction of a bromomagnesium enolate with ketones 5 leads to b-hydroxyesters, which, by appropriate sequences of reduction and cleavage (Scheme II) are converted to optically active a- or b-hydroxy-g-lactones.
.

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The Efficient Synthesis of the Optically Active £]-Hydroxyl-£^-butyrolactone Derivatives
 
Jin Xin Wang, Ying Li* , Chao Xin Zhang
National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000, P. R. China
 
Abstract.     The optically active £]-hydroxyl-£^-butyrolactones were synthesized from nonchiral starting material by employing reductive cleavage reaction, sharpless asymmetric epoxidation and dihydroxylation, and Lewis acid-catalysed cyclization as key steps. This strategy can be used to prepare many chiral b-hydroxyl-g-butyrolactone analogues.

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    Kinetic
(Hive Bee)
08-26-04 22:26
No 527565
      References     

So you've just discovered Journal of the Chinese Chemical Society is available free online?wink Fair enough, but please add the reference for each article you post or link to. This way, it can be easily found in the search engine so in the future others can check if the article has been posted.

BTW, what enantioselectively synthesised butyrolactones are you interested in? The most well known lactone at the Hive, gamma-butyrolactone, does not need to be synthesised by any such complex route as it is achiral.
 
 
 
 
    lutesium
(Newbee)
08-26-04 22:35
No 527571
      :)     

:)

I am REALLY interested in G analogs and I have seen many new drugs that are similar to GABA and GBL having anticonvulsant or antidepressant and mood brightening effects. G is highly intoxicating (for me) but it has an unattainable mood brightening effect. If an analog having the latter charachteristic without the intoxicating effect can be produced it might be a revolution for the legal pharmaceutical market which still makes us use these croaking antidepressants.
 
 
 
 
    java
(Hive Addict)
08-26-04 22:35
No 527572
      Add ref to your articles ....     

Referencing articles for the search engine..example....

Post 517769 (java: "Reduction of Aromatic Nitro Compounds", Novel Discourse)

It is better to die on your feet than to live on your knees.......
-Emiliano Zapata-