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Strychnos 1990 - 2004 - Crops for the Future

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Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Sole, D., J. Bonjoch, S. Garcia-Rubio, E. Peidro and J. Bosch<br />

Enantioselective total syn<strong>the</strong>sis of wieland-gumlich aldehyde and (-)-strychnine<br />

2000<br />

Chemistry- A European Journal<br />

6(4): 655-665<br />

Abstract<br />

A total syn<strong>the</strong>sis of (-)-strychnine in 15 steps from 1,3-cyclohexanedione in 0.15% overall yield is<br />

described. The sequence followed in <strong>the</strong> assembling of rings is: E --> AE [2-(2-nitrophenyl)-1,3-<br />

cyclohexanedione] --> ACE (3a-aryloctahydroindol-4-one) --> ACDE (arylazatricyclic core)<br />

ABCDE (strychnan skeleton) --> ABCDEF (Wieland-Gumlich aldehyde) --> ABCDEFG<br />

(strychnine). The key steps of <strong>the</strong> syn<strong>the</strong>sis are <strong>the</strong> enantioselective construction of <strong>the</strong> 3a-(2-<br />

nitrophenyl)octahydroindol-4-one ring system and <strong>the</strong> closure of <strong>the</strong> piperidine ring by a reductive<br />

Heck cyclization to generate <strong>the</strong> pivotal intermediate (-)-14. In contrast, a Lewis acid promoted<br />

alpha-alkoxy-propargylic silane-enone cyclization did not lead to syn<strong>the</strong>tically useful azatricyclic<br />

ACDE intermediates. The introduction of C-17 and <strong>the</strong> closure of <strong>the</strong> indoline ring by reductive<br />

amination of <strong>the</strong> alpha-(2-nitrophenyl) ketone moiety complete <strong>the</strong> strychnan skeleton from which,<br />

via <strong>the</strong> Wieland-Gumlich aldehyde, <strong>the</strong> syn<strong>the</strong>sis of (-)-strychnine is achieved.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Tripathi, Y. B. and S. Chaurasia<br />

Interaction of <strong>Strychnos</strong> nux vomica-products and iron: With reference to lipid pe<br />

2000<br />

Phytomedicine<br />

7(6): 523-528<br />

Abstract<br />

In this paper, it has been investigated that strychnine, <strong>the</strong> major active principle in <strong>the</strong> alcoholic<br />

extract of <strong>the</strong> seeds of <strong>Strychnos</strong> nux-vomica, is responsible <strong>for</strong> its antilipid peroxidative property.<br />

The mechanism of action of this drug is through <strong>the</strong> chelation of <strong>the</strong> free iron in <strong>the</strong> system. It has<br />

also been observed that strychnine does not have any pro-oxidant-property, because it does not<br />

convert Fe3+ to Fe2+ and vice versa in <strong>the</strong> reaction system, as has been observed with several o<strong>the</strong>r<br />

a n t i o x i d a n t s .

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