Total synthesis of purpurosamine B from D-alanine
β Scribed by Golebiowski, Adam; Jacobsson, Ulla; Raczko, Jerzy; Jurczak, Janusz
- Book ID
- 126821737
- Publisher
- American Chemical Society
- Year
- 1989
- Tongue
- English
- Weight
- 295 KB
- Volume
- 54
- Category
- Article
- ISSN
- 0022-3263
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π SIMILAR VOLUMES
Methyl 2,6-di-I-acetyl-6-epia-&-purpurosaminide B (11) was synthesized from L-alanine by an eleven-step reaction sequence. Eu(fod)a-mediated high-pressure (4t2)cycloaddition of 1-methoxybuta-1,3-diene (2) to a-amino aldehyde 3, easily available from Galanine (A), is the key step in the synthetic seq
6-epi-D-Purpurosamine B was synthesized efficiently through a chiral Z-olefin 8 derived from L-alanine and L-malic acid under complete stereochemical control by using iodocyclocarbamation as the key reaction.
In relation to the synthesis of antipseudomonal drugs, namely, gentamicin C2 and 3-de-O-methylsporaricin A, a protected purpurosamine B (15) and 6-epipurpurosamine B (13) were synthesized. The key intermediate, methyl 2,3,4,7- tetradeoxy-6-O-(methylsulfonyl)-2-phthalimido-beta-L-lyxo-++ +heptopyrano