TY - JOUR
T1 - An Optimized and General Synthetic Strategy To Prepare Arylnaphthalene Lactone Natural Products from Cyanophthalides
AU - Kim, Taejung
AU - Jeong, Kyu Hyuk
AU - Kang, Ki Sung
AU - Nakata, Masaya
AU - Ham, Jungyeob
N1 - Publisher Copyright:
© 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2017/4/3
Y1 - 2017/4/3
N2 - A simple method for the preparation of arylnaphthalene lactone natural products was developed and used to synthesize diphyllin (10), justicidin A (12), cilinaphthalide B (13), taiwanin E (15), chinensinaphthol (16), taiwanin E methyl ether (17), chinensinaphthol methyl ether (18), justicidin C (21), and justicidin D (22). Key steps of the syntheses include the Hauser–Kraus annulation of cyanophthalides 7a and 7b and Suzuki–Miyaura cross-coupling reactions between arylnaphthalene lactones that contain a sulfonate group (i.e., 9, 14, 19, and 20) and various potassium aryltrifluoroborates.
AB - A simple method for the preparation of arylnaphthalene lactone natural products was developed and used to synthesize diphyllin (10), justicidin A (12), cilinaphthalide B (13), taiwanin E (15), chinensinaphthol (16), taiwanin E methyl ether (17), chinensinaphthol methyl ether (18), justicidin C (21), and justicidin D (22). Key steps of the syntheses include the Hauser–Kraus annulation of cyanophthalides 7a and 7b and Suzuki–Miyaura cross-coupling reactions between arylnaphthalene lactones that contain a sulfonate group (i.e., 9, 14, 19, and 20) and various potassium aryltrifluoroborates.
KW - Annulation
KW - Cross-coupling
KW - Lactones
KW - Natural products
KW - Total synthesis
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U2 - 10.1002/ejoc.201601611
DO - 10.1002/ejoc.201601611
M3 - Article
AN - SCOPUS:85017154457
SN - 1434-193X
VL - 2017
SP - 1704
EP - 1712
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
IS - 13
ER -