- The Stereospecific Synthesis of Abscisic Acid
- The Stereospecific Synthesis of Abscisic Acid
- ㆍ 저자명
- Park. Oee-Sook,Lee. W.Y.,Park. J.C.
- ㆍ 간행물명
- 생약학회지
- ㆍ 권/호정보
- 1986년|17권 1호|pp.67-72 (6 pages)
- ㆍ 발행정보
- 한국생약학회
- ㆍ 파일정보
- 정기간행물|ENG| PDF텍스트
- ㆍ 주제분야
- 기타
A stereospecific synthesis of 3-methyl-5-(1-hydroxy-4-oxo-2,6,6-trimethyl-2-cyclohexen-1-yl)-cis, trans-2,4-pentadienoic acid (abscisic acid) from ${alpha}-ionone$ has been investigated. Ethyl 5-(2,6,6-trimetyl-2-cyclohexen-1-yl)-trans-4-penten-2-ynoate $({alpha},{eta}-acetylenic;ester)$, which was synthesized from alpha-ionone in two steps, was stereospecifically converted in good yield into ethyl 3-methyl-5-(2,6,6-trimethyl-2-cyclohexen-1-yl)-cis, trans-2, 4-pentadienoate $({alpha}-ionylideneacetate)$ by the conjugate addition of lithium dimethylcuprate at $-78^{circ}C$. Basic hydrolysis of the ethyl ${alpha}-ionylideneacetate$ gave an abscisic acid precursor, 3-methyl-5-(2,6,6-trimethyl-2-cyclohexen-1-yl)-cis, trans-2,4-pentadienoic acid, which can be oxidized to yield abscisic acid.