TY - JOUR
T1 - A doubly-convergent and regioselective synthesis of (±)-daunomycinone
AU - Tamariz, Joaquin
AU - Vogel, Pierre
N1 - Funding Information:
tation was con6rmed by the regioselectivityo f the electrophilica dditions of the C-C double bonds in bicyclo[2.2.1]hept-5ce-2-onea nd bicyclo[2.2.2]oct-5ene2-one,” and was supported by MO calcu- lations.‘6*1A* s expectedfo r an electronw ithdrawing substituents uch as the dicyanomethylideneg roup which lacks the n electronst hat can interactw ith the aC(1.2)b ond, thec ycloadditionso ftriene1 4t o methyl propynoatew as “meta” regioselectiveC.o ntrastingly, that of the simpler triene 18 showedg ood “para” regioselectivit1y9 . This resulth asb eene xploitedin the developmento f a highly versatiles ynthesiso f (*)-daunomycinone3 which is reportedh ere.
PY - 1984
Y1 - 1984
N2 - The monoadduct of benzoquinone to 2,3,5,6-tetramethylidene-7-oxabicyclo[2.2. l]heptane (7) was transformed into (1RS,4RS,4aSR)-2,3-dimethylidene-l,4-epoxy-l,2,3,4,4a,10-hexahydro-8-methoxyanthracene (28). ‡The exocyclic diene added to methy into (±)-7,9-dideoxydaunomycinone (54), a known precursor of(±)-daunomycinone.
AB - The monoadduct of benzoquinone to 2,3,5,6-tetramethylidene-7-oxabicyclo[2.2. l]heptane (7) was transformed into (1RS,4RS,4aSR)-2,3-dimethylidene-l,4-epoxy-l,2,3,4,4a,10-hexahydro-8-methoxyanthracene (28). ‡The exocyclic diene added to methy into (±)-7,9-dideoxydaunomycinone (54), a known precursor of(±)-daunomycinone.
UR - http://www.scopus.com/inward/record.url?scp=0021680625&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(01)91514-5
DO - 10.1016/S0040-4020(01)91514-5
M3 - Artículo
SN - 0040-4020
VL - 40
SP - 4549
EP - 4560
JO - Tetrahedron
JF - Tetrahedron
IS - 22
ER -