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Synthesis of New Tetracyclic Aristotelia Alkaloids.

✍ Scribed by Md Abul Hashem; Zannatul Ferdoush


Publisher
John Wiley and Sons
Year
2003
Weight
152 KB
Volume
34
Category
Article
ISSN
0931-7597

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✦ Synopsis


Abstract

For Abstract see ChemInform Abstract in Full Text.


📜 SIMILAR VOLUMES


Synthesis of Aristotelia-Type Alkaloids.
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8. XI. 90) (S)-Perilla alcohol (5) was transformed into (S)-7-(phenylthio)-p-menth-l-en-8-amine (11) in five steps. Condensation of this building block with 1 -(4-methoxyphenyIsulfonyl)-l H-indole-3-acetaldehyde (12) led to the expected imine 15 which cyclized in 54% yield to protected 20-(pheny1thi

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## Abstract The probably most straightforward plan to synthesize the indole alkaloid alloaristoteline (5) failed, because– in marked contrast to the regular __Aristotelia__ series‐electrophilic reagents attack with preference C(3) of the indole moiety in the key intermediate allohobartine ((−)‐12),

Synthesis of Aristotelia-Type Alkaloids.
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Part 111: [I]. ') Hobartine (4) has been synthesized by others in racemic [3] [4] and optically activc form [5] Sc hemr 4 CHO dC? dC> OK$ p-M BS p-M BS H 15 18 17 R=CH, Reagents: a) 1. 2 equiv. BuLi, 2. p-methoxybenzenesulfonyl chloride; b) CH,N2; c) DIBAH, -70". ' ) 7,

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Synthetic (+)-makomakine (6) was transformed in six steps into (+)-( 17 R,18R)-17,18-dihydrohobartine-17,18-diol((+)-5) with an overall yield of 38 % (Scheme 2). This compound was shown to be identical with natural hobartinol, a monoterpene indole alkaloid from Aristoteliu uustrulusicu, originally b

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## Abstract Biomimetic syntheses of racemic aristomakinine ((±)‐3) and aristomakine ((±)‐4), an unusual indole alkaloid bearing an __N__‐isopropyl group, are described. The key step is a __Grob__‐type fragmentation of __anti__‐15‐aristotelinyl methanesulfonate ((±)‐2) to the intermediate iminium io