Asymmetric synthesis of acetomycin

S.S. Kinderman; B.L. Feringa

doi:10.1016/S0957-4166(98)00100-1

Asymmetric synthesis of acetomycin

S.S. Kinderman
, B.L. Feringa

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

13 Citations (Scopus)

358 Downloads (Pure)

Abstract

The synthesis of (-)-acetomycin, a highly functionalized γ-lactone with antitumor activity, was achieved in five steps with nearly complete enantioselectivity. The key step was realized by a large scale lipase R catalyzed esterification of 5-hydroxy-4-methyl-2(5H)-furanone providing (-)-(5R)-5-acetoxy-4-methyl-2(5H)-furanone with an e.e. of 99%.

Original language	English
Pages (from-to)	1215 - 1222
Number of pages	8
Journal	Tetrahedron-Asymmetry
Volume	9
Issue number	7
DOIs	https://doi.org/10.1016/S0957-4166(98)00100-1
Publication status	Published - 1998

Keywords

GAMMA-MENTHYLOXYBUTENOLIDES
ENANTIOSELECTIVE SYNTHESIS
1,3-DITHIENIUM FLUOROBORATE
STEREOSELECTIVE SYNTHESIS
TUMOR-CELLS
(+/-)-ACETOMYCIN
(-)-ACETOMYCIN
1,4-ADDITIONS
RESOLUTION
TRANSESTERIFICATION

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@article{8c8ecf0e7b2546c6af171d86aaa1557c,

title = "Asymmetric synthesis of acetomycin",

abstract = "The synthesis of (-)-acetomycin, a highly functionalized γ-lactone with antitumor activity, was achieved in five steps with nearly complete enantioselectivity. The key step was realized by a large scale lipase R catalyzed esterification of 5-hydroxy-4-methyl-2(5H)-furanone providing (-)-(5R)-5-acetoxy-4-methyl-2(5H)-furanone with an e.e. of 99\%.",

keywords = "GAMMA-MENTHYLOXYBUTENOLIDES, ENANTIOSELECTIVE SYNTHESIS, 1,3-DITHIENIUM FLUOROBORATE, STEREOSELECTIVE SYNTHESIS, TUMOR-CELLS, (+/-)-ACETOMYCIN, (-)-ACETOMYCIN, 1,4-ADDITIONS, RESOLUTION, TRANSESTERIFICATION",

author = "S.S. Kinderman and B.L. Feringa",

note = "Relation: http://www.rug.nl/scheikunde/ date\_submitted:2005 Rights: University of Groningen. Stratingh Institute",

year = "1998",

doi = "10.1016/S0957-4166(98)00100-1",

language = "English",

volume = "9",

pages = "1215 -- 1222",

journal = "Tetrahedron-Asymmetry",

issn = "0957-4166",

publisher = "PERGAMON-ELSEVIER SCIENCE LTD",

number = "7",

}

TY - JOUR

T1 - Asymmetric synthesis of acetomycin

AU - Kinderman, S.S.

AU - Feringa, B.L.

N1 - Relation: http://www.rug.nl/scheikunde/ date_submitted:2005 Rights: University of Groningen. Stratingh Institute

PY - 1998

Y1 - 1998

N2 - The synthesis of (-)-acetomycin, a highly functionalized γ-lactone with antitumor activity, was achieved in five steps with nearly complete enantioselectivity. The key step was realized by a large scale lipase R catalyzed esterification of 5-hydroxy-4-methyl-2(5H)-furanone providing (-)-(5R)-5-acetoxy-4-methyl-2(5H)-furanone with an e.e. of 99%.

AB - The synthesis of (-)-acetomycin, a highly functionalized γ-lactone with antitumor activity, was achieved in five steps with nearly complete enantioselectivity. The key step was realized by a large scale lipase R catalyzed esterification of 5-hydroxy-4-methyl-2(5H)-furanone providing (-)-(5R)-5-acetoxy-4-methyl-2(5H)-furanone with an e.e. of 99%.

KW - GAMMA-MENTHYLOXYBUTENOLIDES

KW - ENANTIOSELECTIVE SYNTHESIS

KW - 1,3-DITHIENIUM FLUOROBORATE

KW - STEREOSELECTIVE SYNTHESIS

KW - TUMOR-CELLS

KW - (+/-)-ACETOMYCIN

KW - (-)-ACETOMYCIN

KW - 1,4-ADDITIONS

KW - RESOLUTION

KW - TRANSESTERIFICATION

U2 - 10.1016/S0957-4166(98)00100-1

DO - 10.1016/S0957-4166(98)00100-1

M3 - Article

SN - 0957-4166

VL - 9

SP - 1215

EP - 1222

JO - Tetrahedron-Asymmetry

JF - Tetrahedron-Asymmetry

IS - 7

ER -

Asymmetric synthesis of acetomycin

Abstract

Keywords

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