Abstract:
:Synthesis of (1R,2S,5S,6R,8S)-3-azabicyclo[3.3.0]octane-2,6,8-tricarboxylic acid (2) from trans-4-hydroxy-L-proline (5) was attempted. A Diels-Alder reaction of 3,4-dehydroproline derivative 9 and cyclopentadiene afforded a single stereoisomer 11. The Diels-Alder adduct was smoothly converted to the hydrochloride of 2 (24) via RuO(4) oxidation. Although some racemization of the material or product was observed during the synthetic processes, the amino acid 24 proved to be optically pure.
journal_name
Chem Pharm Bull (Tokyo)journal_title
Chemical & pharmaceutical bulletinauthors
Arakawa Y,Ohnishi M,Yoshimura N,Yoshifuji Sdoi
10.1248/cpb.51.1015subject
Has Abstractpub_date
2003-08-01 00:00:00pages
1015-20issue
8eissn
0009-2363issn
1347-5223journal_volume
51pub_type
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