Srikrishna, A and Danieldoss, S and Venkateswarlu, S and Sattigeri, JA (1997) A formal total synthesis of (+/-)-enterolactone. In: Journal of the Indian Chemical Society, 74 (11-12). pp. 864-869.Full text not available from this repository.
A radical cyclization based methodology has been applied for the formal total synthesis of (+/-)-enterolactone (1), the first lignan isolated from human source. Bromoacetalization reaction of the cinnamyl alcohols 7 and 13 using ethyl vinyl ether and NBS, generated the bromoacetals 8 and 15. The 5-exo-trig radical cyclization reaction of the bromoacetals 8 and 15 with in situ generated catalytic tri-a-butyltin hydride and AIBN furnished a 3 : 2 diastereomeric mixture of the cyclic acetals 9 and 16. Sonochemically accelerated Jones oxidation of the cyclic acetals 9 and 16 yielded the gamma-butyrolactones 10 and 12 completing the formal total synthesis of (+/-)-enterolactone. Alternatively radical cyclization of the bromoacetate 17 furnished a 1 : 2 mixture of the lactone 10 and the reduced product 18.
|Item Type:||Journal Article|
|Additional Information:||Copyright of this article belongs to Indian Chemical Society.|
|Department/Centre:||Division of Chemical Sciences > Organic Chemistry|
|Date Deposited:||19 Oct 2011 07:53|
|Last Modified:||19 Oct 2011 07:53|
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