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Total Synthesis of Angucyclines, 1. – Synthesis of a Daunomycinone–Rabelomycin Hybrid
Author(s) -
Krohn Karsten,
Ballwanz Frank,
Baltus Wolfgang
Publication year - 1993
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1993199301143
Subject(s) - chemistry , solvolysis , halogenation , bromide , yield (engineering) , ketone , stereochemistry , total synthesis , organic chemistry , hydrolysis , materials science , metallurgy
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 .