Formal synthesis of salinosporamide A using a nickel-catalyzed reductive aldol cyclization-lactonization as a key step

Isabel Villanueva Margalef; Leszek Rupnicki; Hon Wai Lam

doi:10.1016/j.tet.2008.06.038

Formal synthesis of salinosporamide A using a nickel-catalyzed reductive aldol cyclization-lactonization as a key step

Isabel Villanueva Margalef, Leszek Rupnicki, Hon Wai Lam

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

Abstract

Application of a sequential nickel-catalyzed reductive aldol cyclization-lactonization reaction in a short formal synthesis of salinsporamide A, a potent 20S proteasome inhibitor and anti-cancer compound, is described. (C) 2008 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	7896-7901
Number of pages	6
Journal	Tetrahedron
Volume	64
Issue number	34
DOIs	https://doi.org/10.1016/j.tet.2008.06.038
Publication status	Published - 18 Aug 2008

Keywords

ENANTIOSELECTIVE TOTAL-SYNTHESIS
POTENT PROTEASOME INHIBITOR
BAYLIS-HILLMAN REACTION
CONCISE TOTAL-SYNTHESIS
STEREOCONTROLLED SYNTHESIS
STOICHIOMETRIC REDUCTANT
MICROBIAL METABOLITE
NEUROBLASTOMA-CELLS
SECONDARY ALCOHOLS
ORGANIC-SYNTHESIS

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10.1016/j.tet.2008.06.038

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title = "Formal synthesis of salinosporamide A using a nickel-catalyzed reductive aldol cyclization-lactonization as a key step",

abstract = "Application of a sequential nickel-catalyzed reductive aldol cyclization-lactonization reaction in a short formal synthesis of salinsporamide A, a potent 20S proteasome inhibitor and anti-cancer compound, is described. (C) 2008 Elsevier Ltd. All rights reserved.",

keywords = "ENANTIOSELECTIVE TOTAL-SYNTHESIS, POTENT PROTEASOME INHIBITOR, BAYLIS-HILLMAN REACTION, CONCISE TOTAL-SYNTHESIS, STEREOCONTROLLED SYNTHESIS, STOICHIOMETRIC REDUCTANT, MICROBIAL METABOLITE, NEUROBLASTOMA-CELLS, SECONDARY ALCOHOLS, ORGANIC-SYNTHESIS",

author = "Margalef, {Isabel Villanueva} and Leszek Rupnicki and Lam, {Hon Wai}",

year = "2008",

month = aug,

day = "18",

doi = "10.1016/j.tet.2008.06.038",

language = "English",

volume = "64",

pages = "7896--7901",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "34",

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TY - JOUR

T1 - Formal synthesis of salinosporamide A using a nickel-catalyzed reductive aldol cyclization-lactonization as a key step

AU - Margalef, Isabel Villanueva

AU - Rupnicki, Leszek

AU - Lam, Hon Wai

PY - 2008/8/18

Y1 - 2008/8/18

N2 - Application of a sequential nickel-catalyzed reductive aldol cyclization-lactonization reaction in a short formal synthesis of salinsporamide A, a potent 20S proteasome inhibitor and anti-cancer compound, is described. (C) 2008 Elsevier Ltd. All rights reserved.

AB - Application of a sequential nickel-catalyzed reductive aldol cyclization-lactonization reaction in a short formal synthesis of salinsporamide A, a potent 20S proteasome inhibitor and anti-cancer compound, is described. (C) 2008 Elsevier Ltd. All rights reserved.

KW - ENANTIOSELECTIVE TOTAL-SYNTHESIS

KW - POTENT PROTEASOME INHIBITOR

KW - BAYLIS-HILLMAN REACTION

KW - CONCISE TOTAL-SYNTHESIS

KW - STEREOCONTROLLED SYNTHESIS

KW - STOICHIOMETRIC REDUCTANT

KW - MICROBIAL METABOLITE

KW - NEUROBLASTOMA-CELLS

KW - SECONDARY ALCOHOLS

KW - ORGANIC-SYNTHESIS

UR - http://www.scopus.com/inward/record.url?scp=46649114726&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2008.06.038

DO - 10.1016/j.tet.2008.06.038

M3 - Article

VL - 64

SP - 7896

EP - 7901

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 34

ER -

Formal synthesis of salinosporamide A using a nickel-catalyzed reductive aldol cyclization-lactonization as a key step

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Total synthesis of salinosporamide a

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Formal synthesis of salinosporamide A using a nickel-catalyzed reductive aldol cyclization-lactonization as a key step

Abstract

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Total synthesis of salinosporamide a

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