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Total Synthesis of Angucyclines, 1. – Synthesis of a Daunomycinone–Rabelomycin Hybrid

✍ Scribed by Krohn, Karsten ;Ballwanz, Frank ;Baltus, Wolfgang

Publisher
John Wiley and Sons
Year
1993
Tongue
English
Weight
339 KB
Volume
1993
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The synthesis of the racemic angucyclinone hybrid 3 which combines the structural features of rabelomycin (1) and daunomycinone (2) is described. Key steps are the cyclization of the bromide 6b by a Marshalk‐type reaction to yield the angular skeleton 7b, introduction of the tertiary hydroxy group by bromination to 11, solvolysis to 12 and photoinduced oxygenation to afford the C‐1 ketone 3.

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