ChemInform Abstract: Synthesis of Trichiliasterones A and B - 16-Ketosteroids Isolated from Trichilia hirta and Trichilia americana.

ChemInform ◽  
2010 ◽  
Vol 33 (25) ◽  
pp. no-no
Author(s):  
Susanne M. Hantos ◽  
Sasmita Tripathy ◽  
Najma Alibhai ◽  
Tony Durst
Keyword(s):  
Trichilia Americana

Synthesis of trichiliasterones A and B — 16-Ketosteroids isolated from Trichilia hirta and Trichilia americana

2001 ◽  
Vol 79 (11) ◽  
pp. 1747-1753 ◽  
Author(s):  
Susanne M. Hantos ◽  
Sasmita Tripathy ◽  
Najma Alibhai ◽  
Tony Durst
Keyword(s):  
Trichilia Americana

Biological Activity of Trichilia americana (Meliaceae) on Copitarsia decolora Guenée (Lepidoptera: Noctuidae)

2019 ◽  
Vol 54 (2) ◽  
pp. 131
Author(s):  
Rodolfo Figueroa Brito ◽  
Elyda Hernández Miranda ◽  
Víctor Rogelio Castrejón Gómez
Keyword(s):  
Biological Activity ◽  
Trichilia Americana ◽  
Lepidoptera Noctuidae

Synthesis of trichiliasterones A and B — 16-Ketosteroids isolated from Trichilia hirta and Trichilia americana

2001 ◽  
Vol 79 (11) ◽  
pp. 1747-1753
Author(s):  
Susanne M Hantos ◽  
Sasmita Tripathy ◽  
Najma Alibhai ◽  
Tony Durst
Keyword(s):  
Double Bond ◽  
Wittig Reaction ◽  
Hydroxyl Group ◽  
Unsaturated Ketone ◽  
Enol Acetate ◽  
Trichilia Americana ◽  
Methylene Group ◽  
Lead Tetra Acetate

The syntheses of trichiliasterone A (3β-hydroxypregnan-2,16-dione) and trichiliasterone B (2-hydroxyandrost-1,4-diene-3,16-dione) have been carried out starting from isoandrosterone and testosterone acetate, respectively. In each synthesis the functionality in the D ring was installed prior to working on ring A. In the case of trichiliasterone A, the D ring chemistry involved a Wittig reaction to generate the 17-methylene group, followed by SeO2 oxidation to give an α,β-unsaturated ketone. Reaction with lithium dimethyl cuprate gave the required 17-ethyl-16-keto functionality. A 2,3-epoxy enol acetate served as the key intermediate for the generation of the 2-keto-3-hydroxy functions in ring A. The transposition of the keto function from C-16 to C-17 in the synthesis of trichiliasterone B was accomplished via oxymercuration–demercuration of the Δ16—17 double bond followed by oxidation. The hydroxyl group at C-2 and the additional ring A unsaturation were introduced by lead tetra-acetate treatment of the 3-keto-4-enone function and subsequent air oxidation.Key words: 16-ketosteroids, plant steroids, Trichilia hirta, trichiliasterones.

Cytotoxic limonoids from Trichilia americana leaves

2015 ◽  
Vol 118 ◽  
pp. 61-67 ◽  
Author(s):  
Kai-Long Ji ◽  
Ping Zhang ◽  
Xiao-Nian Li ◽  
Juan Guo ◽  
Hua-Bin Hu ◽  
...  
Keyword(s):  
Trichilia Americana
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