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

Taejung Kim, Kyu Hyuk Jeong, Ki Sung Kang, Masaya Nakata, Jungyeob Ham

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)1704-1712
Number of pages9
JournalEuropean Journal of Organic Chemistry
Volume2017
Issue number13
DOIs
Publication statusPublished - 2017 Apr 3

Fingerprint

Lactones
Biological Products
Methyl Ethers
ethers
cross coupling
products
sulfonates
potassium
preparation
Potassium
synthesis
justicidin A
taiwanin E

Keywords

  • Annulation
  • Cross-coupling
  • Lactones
  • Natural products
  • Total synthesis

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

An Optimized and General Synthetic Strategy To Prepare Arylnaphthalene Lactone Natural Products from Cyanophthalides. / Kim, Taejung; Jeong, Kyu Hyuk; Kang, Ki Sung; Nakata, Masaya; Ham, Jungyeob.

In: European Journal of Organic Chemistry, Vol. 2017, No. 13, 03.04.2017, p. 1704-1712.

Research output: Contribution to journalArticle

Kim, Taejung ; Jeong, Kyu Hyuk ; Kang, Ki Sung ; Nakata, Masaya ; Ham, Jungyeob. / An Optimized and General Synthetic Strategy To Prepare Arylnaphthalene Lactone Natural Products from Cyanophthalides. In: European Journal of Organic Chemistry. 2017 ; Vol. 2017, No. 13. pp. 1704-1712.
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