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A stereoselective approach to the angucyclinone antibiotics: A total synthesis of the C-1 epimer of (±)-rubiginone B1

✍ Scribed by David S. Larsen; Michael D. Ośhea

Publisher: Elsevier Science
Year: 1993
Tongue: French
Weight: 228 KB
Volume: 34
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)91799-4

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✦ Synopsis

A smzoselective Lewis acid-promoted cycknddition reaction of S-hydroxy-1,4+aphthoquinone and dienol(12) gave a key inttmmiiate (14) which was traqformed into the ti& compound (18) in 35% overall yield.

The discovery of new mmbers of the angucycliaone group of antibiotics' in r#xnt years has stimulated intense interest in this area. Among these compounds are rubiginone Bl(1) and B2 (2)2, which have been shown to potentiate vincristine cytotoxicity, PO-116740 (3)s which has exhibited activity against L1210 lymphocytic leukemia and human colon adenocarcinoma cell lines, and TAN 1085 (SF which has shown angio~nesis inhibitory activity.

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