Short and versatile route to a key intermediate for lactacystin synthesis

Philip C. B. Bulman Page; A. Sazali Hamzah; David C. Leach; Steven M. Allin; David M. Andrews; Gerasimos A. Rassias

doi:10.1021/ol027387q

Short and versatile route to a key intermediate for lactacystin synthesis

Philip C. B. Bulman Page, A. Sazali Hamzah, David C. Leach, Steven M. Allin, David M. Andrews, Gerasimos A. Rassias

Chemistry of Materials and Catalysis

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

34 Citations (Scopus)

Abstract

A key intermediate 14 for the synthesis of lactacystin 1 has been constructed in four steps and 33% overall yield. The key steps involve cyclization of a suitably functionalized glutamic acid derivative and concomitant alkylation of the resulting beta,beta-diketoester system, C-acylation of the cyclic alpha-amidoketone 9, and decarboxylbenzylation of 12. Alkylation of a related beta,beta-diketoester 5 was additionally achieved with several electrophiles.

Original language	English
Pages (from-to)	353-355
Number of pages	3
Journal	Organic Letters
Volume	5
Issue number	3
DOIs	https://doi.org/10.1021/ol027387q
Publication status	Published - 2003

Keywords

PROTEASOME FUNCTION
ANALOGS
D-GLUCOSE
EFFICIENT
BETA-LACTONE
INHIBITION
(+)-LACTACYSTIN

Access to Document

10.1021/ol027387q

Cite this

@article{32051e22ea984da094dc0feba1ce7eff,

title = "Short and versatile route to a key intermediate for lactacystin synthesis",

abstract = "A key intermediate 14 for the synthesis of lactacystin 1 has been constructed in four steps and 33% overall yield. The key steps involve cyclization of a suitably functionalized glutamic acid derivative and concomitant alkylation of the resulting beta,beta-diketoester system, C-acylation of the cyclic alpha-amidoketone 9, and decarboxylbenzylation of 12. Alkylation of a related beta,beta-diketoester 5 was additionally achieved with several electrophiles.",

keywords = "PROTEASOME FUNCTION, ANALOGS, D-GLUCOSE, EFFICIENT, BETA-LACTONE, INHIBITION, (+)-LACTACYSTIN",

author = "{Bulman Page}, {Philip C. B.} and Hamzah, {A. Sazali} and Leach, {David C.} and Allin, {Steven M.} and Andrews, {David M.} and Rassias, {Gerasimos A.}",

year = "2003",

doi = "10.1021/ol027387q",

language = "English",

volume = "5",

pages = "353--355",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "3",

}

TY - JOUR

T1 - Short and versatile route to a key intermediate for lactacystin synthesis

AU - Bulman Page, Philip C. B.

AU - Hamzah, A. Sazali

AU - Leach, David C.

AU - Allin, Steven M.

AU - Andrews, David M.

AU - Rassias, Gerasimos A.

PY - 2003

Y1 - 2003

N2 - A key intermediate 14 for the synthesis of lactacystin 1 has been constructed in four steps and 33% overall yield. The key steps involve cyclization of a suitably functionalized glutamic acid derivative and concomitant alkylation of the resulting beta,beta-diketoester system, C-acylation of the cyclic alpha-amidoketone 9, and decarboxylbenzylation of 12. Alkylation of a related beta,beta-diketoester 5 was additionally achieved with several electrophiles.

AB - A key intermediate 14 for the synthesis of lactacystin 1 has been constructed in four steps and 33% overall yield. The key steps involve cyclization of a suitably functionalized glutamic acid derivative and concomitant alkylation of the resulting beta,beta-diketoester system, C-acylation of the cyclic alpha-amidoketone 9, and decarboxylbenzylation of 12. Alkylation of a related beta,beta-diketoester 5 was additionally achieved with several electrophiles.

KW - PROTEASOME FUNCTION

KW - ANALOGS

KW - D-GLUCOSE

KW - EFFICIENT

KW - BETA-LACTONE

KW - INHIBITION

KW - (+)-LACTACYSTIN

U2 - 10.1021/ol027387q

DO - 10.1021/ol027387q

M3 - Article

SN - 1523-7060

VL - 5

SP - 353

EP - 355

JO - Organic Letters

JF - Organic Letters

IS - 3

ER -