Chemoenzymatic Total Synthesis of (+)- & (−)-cis-Osmundalactone

Fabian Blume; Yu-Chang Liu; Daniel Thiel; Jan Deska

doi:10.1016/j.molcatb.2016.11.010

Chemoenzymatic Total Synthesis of (+)- & (−)-cis-Osmundalactone

Fabian Blume, Yu-Chang Liu, Daniel Thiel, Jan Deska

Department of Chemistry and Materials Science

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

23 Citations (Scopus)

258 Downloads (Pure)

Abstract

Both optical antipodes of the cis-isomers of osmundalactone, a hydroxypyranone natural product and core structure of the angiopterlactones, have been synthesized from acetylfuran in only three steps through a redox cascade utilizing oxidoreductases and transition metal catalysis in a concerted fashion. The key step in this fully catalytic strategy is the enzyme-mediated Achmatowicz reaction via selective furan oxygenation to furnish the pyran core structure.

Original language	English
Pages (from-to)	280-284
Number of pages	5
Journal	Journal of Molecular Catalysis B: Enzymatic
Volume	134
DOIs	https://doi.org/10.1016/j.molcatb.2016.11.010
Publication status	Published - 12 Nov 2016
MoE publication type	A1 Journal article-refereed

Keywords

biocatalysis
natural products
peroxidase
DEHYDROGENASE
oxidative rearrangement
chemoenzymatic

Access to Document

10.1016/j.molcatb.2016.11.010

JMCBE2016Accepted author manuscript, 341 KBLicence: CC BY-NC-ND

Bioeconomy Research Infrastructure
Seppälä, J. (Manager)
School of Chemical Engineering
Facility/equipment: Facility

Cite this

@article{d1b4fb3cc4444869bf7410774e2af542,

title = "Chemoenzymatic Total Synthesis of (+)- & (−)-cis-Osmundalactone",

abstract = "Both optical antipodes of the cis-isomers of osmundalactone, a hydroxypyranone natural product and core structure of the angiopterlactones, have been synthesized from acetylfuran in only three steps through a redox cascade utilizing oxidoreductases and transition metal catalysis in a concerted fashion. The key step in this fully catalytic strategy is the enzyme-mediated Achmatowicz reaction via selective furan oxygenation to furnish the pyran core structure.",

keywords = "biocatalysis, natural products, peroxidase, DEHYDROGENASE, oxidative rearrangement, chemoenzymatic",

author = "Fabian Blume and Yu-Chang Liu and Daniel Thiel and Jan Deska",

year = "2016",

month = nov,

day = "12",

doi = "10.1016/j.molcatb.2016.11.010",

language = "English",

volume = "134",

pages = "280--284",

journal = "Journal of Molecular Catalysis B: Enzymatic",

issn = "1381-1177",

publisher = "Elsevier",

}

TY - JOUR

T1 - Chemoenzymatic Total Synthesis of (+)- & (−)-cis-Osmundalactone

AU - Blume, Fabian

AU - Liu, Yu-Chang

AU - Thiel, Daniel

AU - Deska, Jan

PY - 2016/11/12

Y1 - 2016/11/12

N2 - Both optical antipodes of the cis-isomers of osmundalactone, a hydroxypyranone natural product and core structure of the angiopterlactones, have been synthesized from acetylfuran in only three steps through a redox cascade utilizing oxidoreductases and transition metal catalysis in a concerted fashion. The key step in this fully catalytic strategy is the enzyme-mediated Achmatowicz reaction via selective furan oxygenation to furnish the pyran core structure.

AB - Both optical antipodes of the cis-isomers of osmundalactone, a hydroxypyranone natural product and core structure of the angiopterlactones, have been synthesized from acetylfuran in only three steps through a redox cascade utilizing oxidoreductases and transition metal catalysis in a concerted fashion. The key step in this fully catalytic strategy is the enzyme-mediated Achmatowicz reaction via selective furan oxygenation to furnish the pyran core structure.

KW - biocatalysis

KW - natural products

KW - peroxidase

KW - DEHYDROGENASE

KW - oxidative rearrangement

KW - chemoenzymatic

U2 - 10.1016/j.molcatb.2016.11.010

DO - 10.1016/j.molcatb.2016.11.010

M3 - Article

SN - 1381-1177

VL - 134

SP - 280

EP - 284

JO - Journal of Molecular Catalysis B: Enzymatic

JF - Journal of Molecular Catalysis B: Enzymatic

ER -

Chemoenzymatic Total Synthesis of (+)- & (−)-cis-Osmundalactone

Abstract

Keywords

Access to Document

Fingerprint

Equipment

Bioeconomy Research Infrastructure

Cite this