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A formal total synthesis of (+/-)-enterolactone

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.

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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
Publication: Journal of the Indian Chemical Society
Publisher: Indian Chemical Society
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
URI: http://eprints.iisc.ac.in/id/eprint/38161

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