Formal Total Synthesis of (+)-C9-Deoxyomuralide from L-Leucine Using a Double Sacrificial Chirality Transfer Approach

Philip C. Bulman Page; Ross L. Goodyear; Alexandra E. Horton; Yohan Chan; Rehana Karim; Maria A. O'Connell; Christopher Hamilton; Alexandra M. Z. Slawin; Benjamin R. Buckley; Steven M. Allin

doi:10.1021/acs.joc.7b02078

Formal Total Synthesis of (+)-C9-Deoxyomuralide from L-Leucine Using a Double Sacrificial Chirality Transfer Approach

Philip C. Bulman Page^*, Ross L. Goodyear, Alexandra E. Horton, Yohan Chan, Rehana Karim, Maria A. O'Connell, Christopher Hamilton, Alexandra M. Z. Slawin, Benjamin R. Buckley, Steven M. Allin

^*Corresponding author for this work

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

Abstract

Formal stereocontrolled syntheses of (+/-)- and (+)-C9-deoxyomuralide is reported, constituting one of the shortest routes to the full carbon skeleton reported to date.

Original language	English
Pages (from-to)	12209-12223
Number of pages	15
Journal	The Journal of Organic Chemistry
Volume	82
Issue number	23
Early online date	7 Nov 2017
DOIs	https://doi.org/10.1021/acs.joc.7b02078
Publication status	Published - 1 Dec 2017

Keywords

PROTEASOME INHIBITOR
BETA-LACTONE
MICROBIAL METABOLITE
NEUROBLASTOMA-CELLS
SALINOSPORAMIDE-A
CRYSTAL-STRUCTURE
20S PROTEASOME
LACTACYSTIN
(+)-LACTACYSTIN
APOPTOSIS

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Page, P. C. B., Goodyear, R. L., Horton, A. E., Chan, Y., Karim, R., O'Connell, M. A., Hamilton, C., Slawin, A. M. Z., Buckley, B. R., & Allin, S. M. (2017). Formal Total Synthesis of (+)-C9-Deoxyomuralide from L-Leucine Using a Double Sacrificial Chirality Transfer Approach. The Journal of Organic Chemistry, 82(23), 12209-12223. https://doi.org/10.1021/acs.joc.7b02078

@article{9bb4c1443aa34006b88740a84c99d368,

title = "Formal Total Synthesis of (+)-C9-Deoxyomuralide from L-Leucine Using a Double Sacrificial Chirality Transfer Approach",

abstract = "Formal stereocontrolled syntheses of (+/-)- and (+)-C9-deoxyomuralide is reported, constituting one of the shortest routes to the full carbon skeleton reported to date.",

keywords = "PROTEASOME INHIBITOR, BETA-LACTONE, MICROBIAL METABOLITE, NEUROBLASTOMA-CELLS, SALINOSPORAMIDE-A, CRYSTAL-STRUCTURE, 20S PROTEASOME, LACTACYSTIN, (+)-LACTACYSTIN, APOPTOSIS",

author = "Page, \{Philip C. Bulman\} and Goodyear, \{Ross L.\} and Horton, \{Alexandra E.\} and Yohan Chan and Rehana Karim and O'Connell, \{Maria A.\} and Christopher Hamilton and Slawin, \{Alexandra M. Z.\} and Buckley, \{Benjamin R.\} and Allin, \{Steven M.\}",

note = "This investigation has enjoyed the support of the BBSRC (BB/I015698/1), Charnwood Molecular Ltd., Loughborough University, and the University of East Anglia. We are also indebted to the EPSRC National Mass Spectrometry Facility at Swansea University.",

year = "2017",

month = dec,

day = "1",

doi = "10.1021/acs.joc.7b02078",

language = "English",

volume = "82",

pages = "12209--12223",

journal = "The Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society (ACS)",

number = "23",

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TY - JOUR

T1 - Formal Total Synthesis of (+)-C9-Deoxyomuralide from L-Leucine Using a Double Sacrificial Chirality Transfer Approach

AU - Page, Philip C. Bulman

AU - Goodyear, Ross L.

AU - Horton, Alexandra E.

AU - Chan, Yohan

AU - Karim, Rehana

AU - O'Connell, Maria A.

AU - Hamilton, Christopher

AU - Slawin, Alexandra M. Z.

AU - Buckley, Benjamin R.

AU - Allin, Steven M.

N1 - This investigation has enjoyed the support of the BBSRC (BB/I015698/1), Charnwood Molecular Ltd., Loughborough University, and the University of East Anglia. We are also indebted to the EPSRC National Mass Spectrometry Facility at Swansea University.

PY - 2017/12/1

Y1 - 2017/12/1

N2 - Formal stereocontrolled syntheses of (+/-)- and (+)-C9-deoxyomuralide is reported, constituting one of the shortest routes to the full carbon skeleton reported to date.

AB - Formal stereocontrolled syntheses of (+/-)- and (+)-C9-deoxyomuralide is reported, constituting one of the shortest routes to the full carbon skeleton reported to date.

KW - PROTEASOME INHIBITOR

KW - BETA-LACTONE

KW - MICROBIAL METABOLITE

KW - NEUROBLASTOMA-CELLS

KW - SALINOSPORAMIDE-A

KW - CRYSTAL-STRUCTURE

KW - 20S PROTEASOME

KW - LACTACYSTIN

KW - (+)-LACTACYSTIN

KW - APOPTOSIS

UR - https://www.scopus.com/pages/publications/85036499264

U2 - 10.1021/acs.joc.7b02078

DO - 10.1021/acs.joc.7b02078

M3 - Article

SN - 0022-3263

VL - 82

SP - 12209

EP - 12223

JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

IS - 23

ER -

Formal Total Synthesis of (+)-C9-Deoxyomuralide from L-Leucine Using a Double Sacrificial Chirality Transfer Approach

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Keywords

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