First Total Synthesis of 9-Hydroxy-8H-pyrano[3,2-f]indol-2-one

Tao Wang; Cheng Wang; Jie Zhang; Huaizhen He

doi:10.1002/jhet.2251

First Total Synthesis of 9-Hydroxy-8H-pyrano[3,2-f]indol-2-one

Tao Wang
, Cheng Wang
, Jie Zhang
, Huaizhen He

Health Science Center

Xi'an Jiaotong University

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

6 Scopus citations

Abstract

A simple and efficient approach to synthesize a novel pyrrolocoumarin 9-hydroxy-8H-pyrano[3,2-f]indol-2-one (7) has been described. Starting from vanillin, the key intermediate 7-methoxy-1H-indol-6-yl propiolate (6) was synthesized in six steps. Then, the target compound was obtained by forming pyrone-ring and demethylation simultaneously in one step. A plausible mechanism invoking PtCl₄ catalyzed one-step reaction of cyclization and demethylation was also presented.

Original language	English
Pages (from-to)	1406-1410
Number of pages	5
Journal	Journal of Heterocyclic Chemistry
Volume	52
Issue number	5
DOIs	https://doi.org/10.1002/jhet.2251
State	Published - 1 Sep 2015

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title = "First Total Synthesis of 9-Hydroxy-8H-pyrano[3,2-f]indol-2-one",

abstract = "A simple and efficient approach to synthesize a novel pyrrolocoumarin 9-hydroxy-8H-pyrano[3,2-f]indol-2-one (7) has been described. Starting from vanillin, the key intermediate 7-methoxy-1H-indol-6-yl propiolate (6) was synthesized in six steps. Then, the target compound was obtained by forming pyrone-ring and demethylation simultaneously in one step. A plausible mechanism invoking PtCl4 catalyzed one-step reaction of cyclization and demethylation was also presented.",

author = "Tao Wang and Cheng Wang and Jie Zhang and Huaizhen He",

note = "Publisher Copyright: {\textcopyright} 2014 HeteroCorporation.",

year = "2015",

month = sep,

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doi = "10.1002/jhet.2251",

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T1 - First Total Synthesis of 9-Hydroxy-8H-pyrano[3,2-f]indol-2-one

AU - Wang, Tao

AU - Wang, Cheng

AU - Zhang, Jie

AU - He, Huaizhen

PY - 2015/9/1

Y1 - 2015/9/1

N2 - A simple and efficient approach to synthesize a novel pyrrolocoumarin 9-hydroxy-8H-pyrano[3,2-f]indol-2-one (7) has been described. Starting from vanillin, the key intermediate 7-methoxy-1H-indol-6-yl propiolate (6) was synthesized in six steps. Then, the target compound was obtained by forming pyrone-ring and demethylation simultaneously in one step. A plausible mechanism invoking PtCl4 catalyzed one-step reaction of cyclization and demethylation was also presented.

AB - A simple and efficient approach to synthesize a novel pyrrolocoumarin 9-hydroxy-8H-pyrano[3,2-f]indol-2-one (7) has been described. Starting from vanillin, the key intermediate 7-methoxy-1H-indol-6-yl propiolate (6) was synthesized in six steps. Then, the target compound was obtained by forming pyrone-ring and demethylation simultaneously in one step. A plausible mechanism invoking PtCl4 catalyzed one-step reaction of cyclization and demethylation was also presented.

UR - https://www.scopus.com/pages/publications/84942552920

U2 - 10.1002/jhet.2251

DO - 10.1002/jhet.2251

M3 - 文章

AN - SCOPUS:84942552920

SN - 0022-152X

VL - 52

SP - 1406

EP - 1410

JO - Journal of Heterocyclic Chemistry

JF - Journal of Heterocyclic Chemistry

IS - 5

ER -

First Total Synthesis of 9-Hydroxy-8H-pyrano[3,2-f]indol-2-one

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