KR970042457A - Preparation of Lignan - Google Patents

Preparation of Lignan Download PDF

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Publication number
KR970042457A
KR970042457A KR1019950056794A KR19950056794A KR970042457A KR 970042457 A KR970042457 A KR 970042457A KR 1019950056794 A KR1019950056794 A KR 1019950056794A KR 19950056794 A KR19950056794 A KR 19950056794A KR 970042457 A KR970042457 A KR 970042457A
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South Korea
Prior art keywords
structural formula
compound represented
following structural
represented
prepare
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KR1019950056794A
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Korean (ko)
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KR100376281B1 (en
Inventor
박정호
표성수
이기승
감종식
박병욱
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김준응
주식회사 선경인더스트리
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Priority to KR1019950056794A priority Critical patent/KR100376281B1/en
Publication of KR970042457A publication Critical patent/KR970042457A/en
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Publication of KR100376281B1 publication Critical patent/KR100376281B1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/27—Polyhydroxylic alcohols containing saturated rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

본 발명은 리그난의 제조방법에 관한 것으로서, 더욱 상세하게는 다음 구조식(2)로 표시되는 유제놀(Eugenol)과 다음 구조식(5)로 표시되는 바닐린(Vaniline)을 출발물질로 하여 말초혈액순환기계, 뇌혈류순환기계, 소화기계질환의 예방 및 치료에 유용한 다음 구조식(1)로 표시되는 리그난을 제조하는 방법에 관한 것이다.The present invention relates to a method for preparing lignan, and more specifically, peripheral blood circulation machine using as starting material eugenol represented by the following structural formula (2) and vanillin (Vaniline) represented by the following structural formula (5). The present invention relates to a method for producing lignan represented by the following structural formula (1), which is useful for the prevention and treatment of diseases of the brain, blood circulation, and digestive system.

(2)(5) (2) (5)

(1) (One)

Description

리그난의 제조방법Preparation of Lignan

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

Claims (2)

(가) 다음 구조식(2)로 표시되는 유제놀(Eugenol)를 보론화 및 산화시켜 다음 구조식(3)로 표시되는 화합물을 제조한 다음, 구조식(3)으로 표시되는 화합물을 알칼리금속 탄산염의 존재 하에서 실온에서 반응시켜 다음 구조식(4)로 표시되는 화합물을 제조하고;(A) Boronated and oxidized Eugenol represented by the following structural formula (2) to prepare a compound represented by the following structural formula (3), and then the compound represented by the structural formula (3) in the presence of alkali metal carbonate Reacting at room temperature under the following to prepare a compound represented by the following structural formula (4); (나) 다음 구조식(5)로 표시되는 바닐린(Vaniline)과 t-부틸클로로디메틸실란을 반응시켜 생성된 생성물을 환원시켜 다음 구조식(6)으로 표시되는 화합물을 제조한 다음, 구조식(6)으로 표시되는 화합물을 N-브로모숙신이 미드와 디메틸술파이드로 처리하여 다음 구조식(7)로 표시되는 화합물을 제조하고;(B) reacting vanillin (Vaniline) represented by the following structural formula (5) with t-butylchlorodimethylsilane to reduce the resulting product to prepare a compound represented by the following structural formula (6), and then the structural formula (6) N-bromosuccinate was treated with the compound and dimethyl sulfide to prepare the compound represented by the following structural formula (7); (다) 상기 (가)에서 제조한 구조식(4)로 표시되는 화합물과 상기 (나)에서 제조한 구조식(7)로 표시되는 화합물을 에탄올 용매하에서 에톡시화나트륨으로 처리하고 환류하여 다음 구조식(8)로 표시되는 화합물을 제조하고:(C) The compound represented by formula (4) prepared in (A) and the compound represented by formula (7) prepared in (B) above were treated with sodium ethoxide in an ethanol solvent and refluxed to obtain the following formula (8). To prepare a compound represented by: (라) 상기 구조식(8)로 표시되는 화합물을 알칼리 용액으로 처리하고, 산(acid)으로 중화한 후 환류시킨 다음, 무수 아세트산과 반응시켜 다음 구조식(9)로 표시되는 화합물을 제조하고;(D) treating the compound represented by formula (8) with an alkaline solution, neutralizing with acid, refluxing, and reacting with acetic anhydride to prepare a compound represented by formula (9); (마) 상기 구조식(9)로 표시되는 화합물을 환원시키는 것을 특징으로 하는 다음 구조식(1)로 표시되는 (±)리그난의 제조방법(E) a process for producing (±) lignan represented by the following structural formula (1), characterized by reducing the compound represented by the structural formula (9); (2)(7)(3)(8) (2) (7) (3) (8) (4)(9) (4) (9) (5)(1) (5) (One) (6) (6) 다음 구조식(9)로 표시되는 화합물을 무수 유기용매하에서 (-)-맨톨 및 디시클로헥실 카보디이미드와 반응시켜 다음 구조식(10)으로 표시되는 부분입체이성질체(diastereomer)를 제조하고, 이는 실리카겔 관크로마토그래피에 의해 각각의 부분입체이성질체를 분리한 후, 각각의 부분입체이성질체를 디이소부틸알루미늄하이드라이드와 반응시키는 것을 특징으로 하는 다음 구조식(1)로 표시되는 (+)- 또는 (-)-리그난의 제조방법.The compound represented by the following structural formula (9) is reacted with (-)-manthol and dicyclohexyl carbodiimide under anhydrous organic solvent to prepare a diastereomer represented by the following structural formula (10), which is a silica gel tube. After separation of each diastereomer by chromatography, each diastereomer is reacted with diisobutylaluminum hydride (+)-or (-)-represented by the following structural formula (1): Method for preparing lignans. (9) (9) (10) 10 (1) (One)
KR1019950056794A 1995-12-26 1995-12-26 Method for preparing lignan KR100376281B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1019950056794A KR100376281B1 (en) 1995-12-26 1995-12-26 Method for preparing lignan

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
KR1019950056794A KR100376281B1 (en) 1995-12-26 1995-12-26 Method for preparing lignan

Publications (2)

Publication Number Publication Date
KR970042457A true KR970042457A (en) 1997-07-24
KR100376281B1 KR100376281B1 (en) 2003-09-26

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KR1019950056794A KR100376281B1 (en) 1995-12-26 1995-12-26 Method for preparing lignan

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Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6118734A (en) * 1984-07-06 1986-01-27 Tsumura Juntendo Inc Production of lignan
JPH03287527A (en) * 1990-04-04 1991-12-18 Daicel Chem Ind Ltd Preventive of carcinogenesis
JPH0570402A (en) * 1991-09-13 1993-03-23 Tsumura & Co New lignans, intermediate thereof and production of the same intermediate
US5488134A (en) * 1993-04-16 1996-01-30 Shionogi & Co., Ltd. Preparation of compounds of lignan series

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