An exceptional 5-endo–trig reversal; a convergent synthesis of daunomycinone
- 1 March 1983
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 61 (3) , 637-639
- https://doi.org/10.1139/v83-116
Abstract
A convergent AB + CD route to daunomycinone (1) is described. The AB segment is synthesized from the Diels–Alder adduct (3) of an isobenzofuran and methyl vinyl ketone by means of an unusual 5-endo–trig cleavage (3 → 4). The CD half (9) is combined with the AB by the Kraus annelation technique to provide a 9-deoxy daunomycinone derivative (12a) which is subsequently oxygenated.Keywords
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