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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 44, Number 1
JKCSEZ 44(1)
February 20, 2000 

A Macrocyclization of (2R)-2-(N,N-Ditosylimido) -3-butenyl methyl malonate by Using Palladium Catalyst

팔라듐 촉매를 이용한 (2R)-2-(N,N-Ditosylimido)-3-butenyl methyl malonate의 거대고리화 반응
Gyusoon Kim, Hakjune Rhee

김규순, 이학준
A-factor,(3R)-2-(6-methylheptanoyl)-3-hydroxymethyl-4-butanolide(1)의 전합성을 위하여 선택된 중간체, (2R)-2-(N,N-ditosylimido)-3-butenyl methyl malonate(4)의 Pd(0) 촉매 커플링 반응에서 예상과는 다르게 14각 고리화합물인 bis(2-methoxycarbonyl-(4E)-hexenolide)(15)가 생성되었다. 이 화합물은 X-ray 결정학을 이용하여 구조를 확인하였다. 이 결과는 다양한 크기의 대칭적인 거대고리화합물을 합성할 수 있다는 것을 제시해 주고 있다.

Upon Pd(0)-catalyzed coupling reaction of (2R)-2-(N,N-ditosylimido)-3-butenyl methyl malonate (4) which was selected for the total synthesis of A-factor, (3R)-2-(6-methylheptanoyl)-3-hydroxy methyl-4-buttinolide (1), an unexpected 14-membered cyclic compound, bis(2-methoxycabonyl-(4E)-hexenolide) (15) was obtained. The structure of this compound was conformed by X-ray crystallography. This result implies that this method can be applied the synthesis of various size of symmetrical macrocyclic compounds.

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