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6-히드록시알킬리덴페니실란산 염의 합성

Synthesis of 6-Hydroxyalkylidenepenicillanates

대한화학회지 1999년 43권 4호 p.447 ~ 455
이종환, 고재영, 서경재, 구양모, 이윤영,
소속 상세정보
이종환 ( Lee Jung-Hwan ) - Seoul National University Department of Chemistry
고재영 ( Ko Jae-Young ) - Seoul National University Department of Chemistry
서경재 ( Seo Kyung-Jae ) - Seoul National University Department of Chemistry
구양모 ( Goo Yang-Mo ) - Seoul National University Deptarment of Pharmacy
이윤영 (  ) - Seoul National University Department of Chemistry

Abstract

Allyl (5R)-dibromopenicillanate(6)의 2,3-O-isopropylidene-D-glyceraldehyde와의 축합, Zn-NH4OAc에 의한 환원 및 Mitsunobu 제거반응의 일련의 과정을 거처서 allyl (5R)-(Z) 및 (5R)-(E)-6-[(2S)-2,3-isopropylidenedioxypropylidene]penicillanate(10a 및 10b)를 합성하였다. 화합물10a의 이소프로필리덴 및 알릴 보호기를 제거하여 potassium (5R)-(Z)-6-[(2S)-2,3-dihydroxypropylidene]penicilla-nate(4)를 얻었다. 그러나 화합물 1Ob의 이소프로필리덴 보호기를 제거한 결과 α,β-unsaturated-Υ-lactone(12)이 얻어짐을 확인하였다. Allyl(5R)-6,6-dibromopenicillanate(6)의 (2S)-2-(t-butyldimethyl-silyloxy)propanal(15)과의 축합, Zn-NH4OAc에 의한 환원 및 Mitsunobu 제거반응 또는 메실화-제거반응의 일련의 과정을 거처서 allyl (5R)-(Z)- 및 (5R)-(E)-6-[(2S)-2-(t-butyldimethylsilyloxy)propylidene]-penicillanate(18a 및 18b)를 합성하였다. 화합물 18a 및 18b의 t-부틸디메틸실릴 및 알릴 보호기를 제거하여 potassium (5R)-(Z)- 및 (5R)-(E)-6-[(2S)-2-hydroxypropylidene]penillanate(5a 및 5b)를 얻었다.

Allyl(5R)-(Z)- and (5R)-(E)-6-[(2S)-2,3-isopropylidenedioxypropylidene]Penicillanate(10a and 10b) were prepared from allyl (5R)-dibromopenicillanate(6) via a sequence of reactions involving condensation with 2,3-O-isopropylidene-D-glyceraldehyde, reduction with Zn-NH4OAc, and Mitsunobuelimination. Deprotection of isopropylidene and allyl groups of l0a gave potassium (5R)-(Z)-6-[(2S)-2,3-dihydroxypropylidene]penicillanate(4) However, deprotection of isopropylidene group of 1Ob afforded α,β-unsaturated-Υ-lactone(12). Allyl (5R)-(Z)- and (5R)-(E)-6-[(2S)-2-(t-butyldimethlsilyloxy)propylidene]penicillanate(18a and 18b) were prepared from ally (5R)-dibromopenicillanate(6) via a sequence of reactions involving condensation with (2S)-2-(t-butyldimethylsilyloxy)propanal(15), reduction with Zn-NH4OAc and Mitsunobu elimination or mesylation-elimination. Deprotection of t-butyldimethylsilyl and allyl groups of 18a and 18b gave potassium (5R)-(Z)- and (5R)-(E)-6-[(2S)-2-hydroxypropylidene]penicillanate(5a and 5b),respectively.

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