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Synthesis of (±)-4-Demethoxydaunomycinone by Double Diels-Alder Additions to 2, 3, 5, 6-Tetramethylidene-7-oxanorbornane

✍ Scribed by Yvonne Bessière; Pierre Vogel

Publisher: John Wiley and Sons
Year: 1980
Tongue: German
Weight: 782 KB
Volume: 63
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19800630123

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✦ Synopsis

Abstract

Sequential Diels‐Alder additions of methylvinyl ketone and dehydrobenzene to 2, 3, 5, 6‐tetramethylidene‐7‐oxanorbornane (4) yielded the (5, 12‐epoxy‐1, 2, 3, 4, 5, 6, 11, 12‐octahydro‐2‐naphtacenyl) methyl ketone (10) which, in few steps was oxidized to a precursos of (±)‐4‐demethoxydaunomycinone. The preparations of two precursors of anthracyclinones, the (5‐acetoxy‐) and (12‐acetoxy‐1, 2, 3, 4‐tetrahydro‐2‐naphtacenyl) methyl ketones (14, 15) are presented. The synthesis of 6, 13‐epoxy‐6, 13‐dihydropentacene (8) is also reported.

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