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An Optimized and General Synthetic Strategy To Prepare Arylnaphthalene Lactone Natural Products from Cyanophthalides
Author(s) -
Kim Taejung,
Jeong Kyu Hyuk,
Kang Ki Sung,
Nakata Masaya,
Ham Jungyeob
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601611
Subject(s) - chemistry , annulation , lactone , ether , sulfonate , potassium , total synthesis , organic chemistry , stereochemistry , catalysis , sodium
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.