The use of 3-acetoxy-1-trimethylsilylbutadiene in the synthesis of anthracyclinone derivatives
- 1 January 1984
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 8,p. 1847-1858
- https://doi.org/10.1039/p19840001847
Abstract
The Diels–Alder reaction of quinizarin quinone (14) with 3-acetoxy-1-trimethylsilylbutadiene (15) affords a tetracyclic adduct, (±)-3-acetoxy-1,4,4aα,12aα-tetrahydro-1β-trimethylsilylnaphthacene-5,6,11,12-tetraone (16) in excellent yield. The simultaneous introduction of the C-7 trimethylsilyl substituent in this process allowed later ready conversion into a C-7 acetoxy group by treatment with lead tetra-acetate. The tetracyclic compound (16) was converted in a convenient multistep process into 4-demethoxydaunomycinone (51) in 41% overall yield from (14). Compound (51) was further elaborated to 14-acetoxy-4-demethoxydaunomycinone (4) by standard reactions, again in good yield (70% overall).This publication has 6 references indexed in Scilit:
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