Synthesis of Bisflavanol-Type Natural Products and Their Analogues via Self-Coupling of C8-Methylol Catechin Derivatives

Deng Ming Huang; Hui Jing Li; Yan Zhao; Yan Chao Wu

doi:10.1055/s-0037-1610707

Synthesis of Bisflavanol-Type Natural Products and Their Analogues via Self-Coupling of C8-Methylol Catechin Derivatives

Deng Ming Huang
, Hui Jing Li^*
, Yan Zhao
, Yan Chao Wu

^*Corresponding author for this work

School of Marine Science and Technology, Harbin Institute of Technology Weihai
CAS - Institute of Chemistry

Research output: Contribution to journal › Article › peer-review

1 Scopus citations

Abstract

A highly efficient and regioselective self-coupling of C8-methylol catechin derivatives is developed for the synthesis of dimeric flavanol analogues under metal-free and mild conditions. Its applicability is showcased by the efficient synthesis of bisflavanol-type natural products bis-8,8′-catechinylmethane, bis-8,8′-epicatechinylmethane, talienbisflavan A, and oolonghomobisflavan A. The novel self-coupling mechanism sheds new light on the classical Friedel-Crafts alkylation mechanism in acid-catalyzed catechin-formaldehyde condensation.

Original language	English
Pages (from-to)	3127-3141
Number of pages	15
Journal	Synthesis (Germany)
Volume	51
Issue number	16
DOIs	https://doi.org/10.1055/s-0037-1610707
State	Published - 31 Jul 2019
Externally published	Yes

Keywords

bis-flavanol
catechin
metal-free
regioselective
self-coupling

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10.1055/s-0037-1610707

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title = "Synthesis of Bisflavanol-Type Natural Products and Their Analogues via Self-Coupling of C8-Methylol Catechin Derivatives",

abstract = "A highly efficient and regioselective self-coupling of C8-methylol catechin derivatives is developed for the synthesis of dimeric flavanol analogues under metal-free and mild conditions. Its applicability is showcased by the efficient synthesis of bisflavanol-type natural products bis-8,8′-catechinylmethane, bis-8,8′-epicatechinylmethane, talienbisflavan A, and oolonghomobisflavan A. The novel self-coupling mechanism sheds new light on the classical Friedel-Crafts alkylation mechanism in acid-catalyzed catechin-formaldehyde condensation.",

keywords = "bis-flavanol, catechin, metal-free, regioselective, self-coupling",

author = "Huang, \{Deng Ming\} and Li, \{Hui Jing\} and Yan Zhao and Wu, \{Yan Chao\}",

note = "Publisher Copyright: {\textcopyright} Georg Thieme Verlag Stuttgart New York.",

year = "2019",

month = jul,

day = "31",

doi = "10.1055/s-0037-1610707",

language = "英语",

volume = "51",

pages = "3127--3141",

journal = "Synthesis (Germany)",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "16",

}

TY - JOUR

T1 - Synthesis of Bisflavanol-Type Natural Products and Their Analogues via Self-Coupling of C8-Methylol Catechin Derivatives

AU - Huang, Deng Ming

AU - Li, Hui Jing

AU - Zhao, Yan

AU - Wu, Yan Chao

N1 - Publisher Copyright: © Georg Thieme Verlag Stuttgart New York.

PY - 2019/7/31

Y1 - 2019/7/31

N2 - A highly efficient and regioselective self-coupling of C8-methylol catechin derivatives is developed for the synthesis of dimeric flavanol analogues under metal-free and mild conditions. Its applicability is showcased by the efficient synthesis of bisflavanol-type natural products bis-8,8′-catechinylmethane, bis-8,8′-epicatechinylmethane, talienbisflavan A, and oolonghomobisflavan A. The novel self-coupling mechanism sheds new light on the classical Friedel-Crafts alkylation mechanism in acid-catalyzed catechin-formaldehyde condensation.

AB - A highly efficient and regioselective self-coupling of C8-methylol catechin derivatives is developed for the synthesis of dimeric flavanol analogues under metal-free and mild conditions. Its applicability is showcased by the efficient synthesis of bisflavanol-type natural products bis-8,8′-catechinylmethane, bis-8,8′-epicatechinylmethane, talienbisflavan A, and oolonghomobisflavan A. The novel self-coupling mechanism sheds new light on the classical Friedel-Crafts alkylation mechanism in acid-catalyzed catechin-formaldehyde condensation.

KW - bis-flavanol

KW - catechin

KW - metal-free

KW - regioselective

KW - self-coupling

UR - https://www.scopus.com/pages/publications/85073893874

U2 - 10.1055/s-0037-1610707

DO - 10.1055/s-0037-1610707

M3 - 文章

AN - SCOPUS:85073893874

SN - 0039-7881

VL - 51

SP - 3127

EP - 3141

JO - Synthesis (Germany)

JF - Synthesis (Germany)

IS - 16

ER -

Synthesis of Bisflavanol-Type Natural Products and Their Analogues via Self-Coupling of C8-Methylol Catechin Derivatives

Abstract

Keywords

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