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

doi:10.1002/ejoc.201601611

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

応用化学科

研究成果: Article › 査読

20 被引用数 (Scopus)

抄録

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.

本文言語	English
ページ（範囲）	1704-1712
ページ数	9
ジャーナル	European Journal of Organic Chemistry
巻	2017
号	13
DOI	https://doi.org/10.1002/ejoc.201601611
出版ステータス	Published - 2017 4月 3

ASJC Scopus subject areas

物理化学および理論化学
有機化学

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10.1002/ejoc.201601611

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title = "An Optimized and General Synthetic Strategy To Prepare Arylnaphthalene Lactone Natural Products from Cyanophthalides",

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.",

keywords = "Annulation, Cross-coupling, Lactones, Natural products, Total synthesis",

author = "Taejung Kim and Jeong, \{Kyu Hyuk\} and Kang, \{Ki Sung\} and Masaya Nakata and Jungyeob Ham",

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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

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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UR - https://www.scopus.com/pages/publications/85017154457#tab=citedBy

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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 -

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

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