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A Novel Rearrangement of Talatisamine Derivatives

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Abstract:

Treatment of talatisamine (1) with 6.5% HBr-HOAc at 80°C for 17h gave the desired 8,14,16,18-tetraacetyltalatisamine (2) (81%). Selective hydrolysis of 2 in dioxane-H2O (1:1) under fluxing condition afforded compound 5 (97%). One-pot treatment of 5 with SOCl2-C6H6 at room temperature overnight followed by evaporation to dryness afforded a residue, which reacted with NaBH4 overnight in THF at 50°C to produce the rearrangement alkaloid 8 (10%) besides the expected 7,17-seco products 6 (45%) and 7 (31%).

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Periodical:

Advanced Materials Research (Volumes 554-556)

Pages:

1664-1668

DOI:

https://doi.org/10.4028/www.scientific.net/AMR.554-556.1664

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Online since:

July 2012

Authors:

Hong Ji, Mu Yuan

Keywords:

8-Chloro Derivatives, C19-Diterpenoid Alkaloid, Skeletal Rearrangement, Talatisamine

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© 2012 Trans Tech Publications Ltd. All Rights Reserved

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