Tetrahedron p. 4569 - 4578 (1984)
Update date:2022-08-04
Topics:
Kelly, T. Ross
Ananthasubramanian, L.
Borah, Kripinath
Gillard, John W.
Goerner, Richard N.
et al.
The development of a general strategy for the control of regiochemistry in the Diels-Alder reactions of substituted naphthazarins is described.Application of this strategy to the synthesis of (+/-)-daunomycinone (2) employs two successive regiochemically controlled Diels-Alder reactions and leads to a ten-step, regiospecific synthesis of (+/-)-2 in 36percent overall yield (Scheme 4).
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