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Synthesis of the tricyclic triamine core of martinelline and martinellic acid

✍ Scribed by Barry B. Snider; Yong Ahn; Bruce M. Foxman

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 247 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(99)00461-x

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✦ Synopsis

The tricyclic triamine core 27 of martinellic acid (2) has been prepared stereospecifically in eight steps from 2-hydroxymethylaniline in 11% overall yield. The key steps are the addition of 2hydroxymethylaniline to vinylcyclopropane 14 to prepare cycloaddition precursor 19 in only two steps and an intramolecular [3+2] azomethine ylide cycloaddition reaction to produce tetracycle 2 0 with >9:1 diastereoselectivity.

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