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

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 -