An Optimized and General Synthetic Strategy To Prepare Arylnaphthalene Lactone Natural Products from Cyanophthalides | Zendy

Kim Taejung | Zendy; Jeong Kyu Hyuk | Zendy; Kang Ki Sung | Zendy; Nakata Masaya | Zendy; Ham Jungyeob | Zendy

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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.

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