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A new synthesis of [26,28-2H6]brassinolide and [26,28-2H6]castasterone via an unusual methyl migration

✍ Scribed by A. Kolbe; A. Porzel; J. Schmidt; G. Adam

Book ID: 102373185
Publisher: John Wiley and Sons
Year: 2003
Tongue: French
Weight: 122 KB
Volume: 46
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.662

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✦ Synopsis

Deuterium-labelled brassinosteroids, namely ½26; 28-2 H 6 castasterone, 8, and ½26; 28-2 H 6 brassinolide, 9, were synthesized starting from 6; 6ethylenedioxy-20-formyl-2a; 3a-isopropylidenedioxy-5a-pregnane, 1, and 3-½ 2 H 3 methyl-but-1-yne-½4; 4; 4-2 H 3 , 11. Upon alkylating cleavage of the epoxide 6 with trimethylaluminium-n-butyllithium an unusual migration of a neighbouring ½ 2 H 3 methyl group takes place to afford deuteriation at positions 26 and 28.

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