Title:
SYNTHESIS METHOD FOR POLYSUBSTITUTED 3-HYDROXY-2-PYRONE
Document Type and Number:
WIPO Patent Application WO/2023/082429
Kind Code:
A1
Abstract:
The present invention relates to a synthesis method for a polysubstituted 3-hydroxy-2-pyrone. The method comprises the following steps: S1, subjecting a compound of formula (I) to an Achmatowicz rearrangement reaction to obtain a compound of formula (II); S2, subjecting the compound of formula (II) to protection by a protecting group, a substitution reaction, an oxidation rearrangement reaction, a carbonyl reduction reaction, protection group removal and an oxidation reaction to obtain the compound of formula (VIII); and S3, subjecting the compound of formula (VIII) to a coupling reaction or a Claisen rearrangement reaction to obtain a compound of formula (IX). According to the method of the present invention, on the basis of introducing a R1 substituent at the 6-position, a R2 substituent can be introduced at the 5-position in a high-selectivity manner by means of the protection by a protecting group and multiple oxidation-reduction, and then a R3 substituent is substituted at the 4-position. The whole operation is convenient and fast, without involving operations such as anhydrous and anaerobic operations, and the substrate has universality, achieving the purpose of synthesizing the polysubstituted 3-hydroxy-2-pyrone at a yield.
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Inventors:
WANG JIAN (CN)
Application Number:
PCT/CN2021/139713
Publication Date:
May 19, 2023
Filing Date:
December 20, 2021
Export Citation:
Assignee:
UNIV TAIZHOU (CN)
International Classes:
C07D309/38; C07F7/08
Domestic Patent References:
| WO2021211982A2 | 2021-10-21 |
Foreign References:
| JP2004203783A | 2004-07-22 |
Other References:
WANG JIAN, MÁRQUEZ-CADENA MIGUEL ADRIÁN, TONG RONGBIAO: "Asymmetric Total Syntheses of (+)-Penostatins A and C", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 22, no. 13, 2 July 2020 (2020-07-02), US , pages 5074 - 5078, XP093066738, ISSN: 1523-7060, DOI: 10.1021/acs.orglett.0c01649
ISOBE MINORU, CHANG WEI-CHUNG, TSOU PEI-KANG, PLOYSUK CHATCHAWAN, YU CHIN-HUI: "Stereochemical Course of Wittig Rearrangements of Dihydropyran Allyl Propargyl Ethers", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 80, no. 12, 19 June 2015 (2015-06-19), pages 6222 - 6237, XP093066741, ISSN: 0022-3263, DOI: 10.1021/acs.joc.5b00678
ZHAO ZHAIHAI, DING WANJING, WANG PIN-MEI, ZHENG DAOQIONG, XU JINZHONG: "Five polyketides isolated from the marine-derived fungus Arthrinium Sp.", NATURAL PRODUCT RESEARCH, TAYLOR AND FRANCIS HEALTH SCIENCES, ABINGDON, GB, vol. 35, no. 15, 3 August 2021 (2021-08-03), GB , pages 2470 - 2475, XP093066745, ISSN: 1478-6419, DOI: 10.1080/14786419.2019.1680663
OKADA MASAHIRO, ITO SATOKO, MATSUBARA AKIRA, IWAKURA IZUMI, EGOSHI SYUSUKE, UEDA MINORU: "Total syntheses of coronatines by exo-selective Diels–Alder reaction and their biological activities on stomatal opening", ORGANIC & BIOMOLECULAR CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, vol. 7, no. 15, 27 May 2009 (2009-05-27), pages 3065 - 3073, XP093066747, ISSN: 1477-0520, DOI: 10.1039/b905159g
GILCHRIST T. L., C.W. REES: "Synthesis of 3-bromo-2-pyrones and their reactions with bases", J. CHEM. SOC. C, 1 January 1968 (1968-01-01), pages 769 - 775, XP093066753
FITZSIMMONS B. J., PLAUMANN D. E., FRASER‐REID B.: "CHIRAL SYNTHONS FOR THE MULTISTRIATINS", CHEMISCHER INFORMATIONSDIENST, vol. 41, 1 January 1979 (1979-01-01), pages 3925 - 3928, XP093066761, ISSN: 0009-2975, DOI: 10.1002/chin.198004359
ISOBE MINORU, CHANG WEI-CHUNG, TSOU PEI-KANG, PLOYSUK CHATCHAWAN, YU CHIN-HUI: "Stereochemical Course of Wittig Rearrangements of Dihydropyran Allyl Propargyl Ethers", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 80, no. 12, 19 June 2015 (2015-06-19), pages 6222 - 6237, XP093066741, ISSN: 0022-3263, DOI: 10.1021/acs.joc.5b00678
ZHAO ZHAIHAI, DING WANJING, WANG PIN-MEI, ZHENG DAOQIONG, XU JINZHONG: "Five polyketides isolated from the marine-derived fungus Arthrinium Sp.", NATURAL PRODUCT RESEARCH, TAYLOR AND FRANCIS HEALTH SCIENCES, ABINGDON, GB, vol. 35, no. 15, 3 August 2021 (2021-08-03), GB , pages 2470 - 2475, XP093066745, ISSN: 1478-6419, DOI: 10.1080/14786419.2019.1680663
OKADA MASAHIRO, ITO SATOKO, MATSUBARA AKIRA, IWAKURA IZUMI, EGOSHI SYUSUKE, UEDA MINORU: "Total syntheses of coronatines by exo-selective Diels–Alder reaction and their biological activities on stomatal opening", ORGANIC & BIOMOLECULAR CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, vol. 7, no. 15, 27 May 2009 (2009-05-27), pages 3065 - 3073, XP093066747, ISSN: 1477-0520, DOI: 10.1039/b905159g
GILCHRIST T. L., C.W. REES: "Synthesis of 3-bromo-2-pyrones and their reactions with bases", J. CHEM. SOC. C, 1 January 1968 (1968-01-01), pages 769 - 775, XP093066753
FITZSIMMONS B. J., PLAUMANN D. E., FRASER‐REID B.: "CHIRAL SYNTHONS FOR THE MULTISTRIATINS", CHEMISCHER INFORMATIONSDIENST, vol. 41, 1 January 1979 (1979-01-01), pages 3925 - 3928, XP093066761, ISSN: 0009-2975, DOI: 10.1002/chin.198004359
Attorney, Agent or Firm:
HANGZHOU SAIKE PATENT AGENCY FIRM (GENERAL PARTNERSHIP) (CN)
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