Preparation of (±)-(erythro)-and (±)-(threo)-2-vinyl citric acids as potential mechanism-based inhibitors of ATP-citrate lyase

Roland E. Dolle; Riccardo Novelli; Barbara A. Saxty; Timothy N.C. Wells; Lawrence I. Kruse; Patrick Camilleri; Drake Eggleston

doi:10.1016/0040-4039(91)80046-9

Preparation of (±)-(erythro)-and (±)-(threo)-2-vinyl citric acids as potential mechanism-based inhibitors of ATP-citrate lyase

Roland E. Dolle
, Riccardo Novelli
, Barbara A. Saxty
, Timothy N.C. Wells
, Lawrence I. Kruse
, Patrick Camilleri
, Drake Eggleston

Research output: Contribution to journal › Article › peer-review

8 Scopus citations

Abstract

The dianion of diethyl-1,3-acetone dicarboxylate 6 was reacted with a vinyl cation equivalent, 2-bromoethyl phenyl selenide, to give the mono alkylated 3-oxoglutarate 7 in 80% yield. Subsequent four-step elaboration gave the title citric acid analogues. These agents were designed as potential mechanism-based inhibitors of ATP-citrate lyase, an enzyme involved in cholesterol and lipid biosynthesis.

Original language	English
Pages (from-to)	4587-4590
Number of pages	4
Journal	Tetrahedron Letters
Volume	32
Issue number	35
DOIs	https://doi.org/10.1016/0040-4039(91)80046-9
State	Published - 1991

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title = "Preparation of (±)-(erythro)-and (±)-(threo)-2-vinyl citric acids as potential mechanism-based inhibitors of ATP-citrate lyase",

abstract = "The dianion of diethyl-1,3-acetone dicarboxylate 6 was reacted with a vinyl cation equivalent, 2-bromoethyl phenyl selenide, to give the mono alkylated 3-oxoglutarate 7 in 80\% yield. Subsequent four-step elaboration gave the title citric acid analogues. These agents were designed as potential mechanism-based inhibitors of ATP-citrate lyase, an enzyme involved in cholesterol and lipid biosynthesis.",

author = "Dolle, \{Roland E.\} and Riccardo Novelli and Saxty, \{Barbara A.\} and Wells, \{Timothy N.C.\} and Kruse, \{Lawrence I.\} and Patrick Camilleri and Drake Eggleston",

year = "1991",

doi = "10.1016/0040-4039(91)80046-9",

language = "English",

volume = "32",

pages = "4587--4590",

journal = "Tetrahedron Letters",

issn = "0040-4039",

number = "35",

}

TY - JOUR

T1 - Preparation of (±)-(erythro)-and (±)-(threo)-2-vinyl citric acids as potential mechanism-based inhibitors of ATP-citrate lyase

AU - Dolle, Roland E.

AU - Novelli, Riccardo

AU - Saxty, Barbara A.

AU - Wells, Timothy N.C.

AU - Kruse, Lawrence I.

AU - Camilleri, Patrick

AU - Eggleston, Drake

PY - 1991

Y1 - 1991

N2 - The dianion of diethyl-1,3-acetone dicarboxylate 6 was reacted with a vinyl cation equivalent, 2-bromoethyl phenyl selenide, to give the mono alkylated 3-oxoglutarate 7 in 80% yield. Subsequent four-step elaboration gave the title citric acid analogues. These agents were designed as potential mechanism-based inhibitors of ATP-citrate lyase, an enzyme involved in cholesterol and lipid biosynthesis.

AB - The dianion of diethyl-1,3-acetone dicarboxylate 6 was reacted with a vinyl cation equivalent, 2-bromoethyl phenyl selenide, to give the mono alkylated 3-oxoglutarate 7 in 80% yield. Subsequent four-step elaboration gave the title citric acid analogues. These agents were designed as potential mechanism-based inhibitors of ATP-citrate lyase, an enzyme involved in cholesterol and lipid biosynthesis.

UR - https://www.scopus.com/pages/publications/0025884649

U2 - 10.1016/0040-4039(91)80046-9

DO - 10.1016/0040-4039(91)80046-9

M3 - Article

AN - SCOPUS:0025884649

SN - 0040-4039

VL - 32

SP - 4587

EP - 4590

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 35

ER -

Preparation of (±)-(erythro)-and (±)-(threo)-2-vinyl citric acids as potential mechanism-based inhibitors of ATP-citrate lyase

Abstract

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