Stereoselective oxidations of a β-methylglycal, anhydrodihydroartemisinin

Yu Ming Pu; Boris Yagen; Herman Ziffer

doi:10.1016/S0040-4039(00)76777-3

Stereoselective oxidations of a β-methylglycal, anhydrodihydroartemisinin

Yu Ming Pu^*, Boris Yagen, Herman Ziffer

^*Corresponding author for this work

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

19 Scopus citations

Abstract

Anhydrodihydroartemisinin (1) was epoxidized with MCPBA-2KF and the resulting 11β,12β-epoxide (2) treated with acidic aqueous acetone to yield 11β-hydroxydihydroepiartemisinin (5). The major product of the reaction of 1 with catalytic quantities of osmium tetroxide using NMO as a co-oxidant was 11α-hydroxydihydroartemisinin (4). Both 4 and 5 were oxidized to the corresponding 11-hydroxyartemisinins.

Original language	English
Pages (from-to)	2129-2132
Number of pages	4
Journal	Tetrahedron Letters
Volume	35
Issue number	14
DOIs	https://doi.org/10.1016/S0040-4039(00)76777-3
State	Published - 4 Apr 1994
Externally published	Yes

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title = "Stereoselective oxidations of a β-methylglycal, anhydrodihydroartemisinin",

abstract = "Anhydrodihydroartemisinin (1) was epoxidized with MCPBA-2KF and the resulting 11β,12β-epoxide (2) treated with acidic aqueous acetone to yield 11β-hydroxydihydroepiartemisinin (5). The major product of the reaction of 1 with catalytic quantities of osmium tetroxide using NMO as a co-oxidant was 11α-hydroxydihydroartemisinin (4). Both 4 and 5 were oxidized to the corresponding 11-hydroxyartemisinins.",

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doi = "10.1016/S0040-4039(00)76777-3",

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AU - Pu, Yu Ming

AU - Yagen, Boris

AU - Ziffer, Herman

PY - 1994/4/4

Y1 - 1994/4/4

N2 - Anhydrodihydroartemisinin (1) was epoxidized with MCPBA-2KF and the resulting 11β,12β-epoxide (2) treated with acidic aqueous acetone to yield 11β-hydroxydihydroepiartemisinin (5). The major product of the reaction of 1 with catalytic quantities of osmium tetroxide using NMO as a co-oxidant was 11α-hydroxydihydroartemisinin (4). Both 4 and 5 were oxidized to the corresponding 11-hydroxyartemisinins.

AB - Anhydrodihydroartemisinin (1) was epoxidized with MCPBA-2KF and the resulting 11β,12β-epoxide (2) treated with acidic aqueous acetone to yield 11β-hydroxydihydroepiartemisinin (5). The major product of the reaction of 1 with catalytic quantities of osmium tetroxide using NMO as a co-oxidant was 11α-hydroxydihydroartemisinin (4). Both 4 and 5 were oxidized to the corresponding 11-hydroxyartemisinins.

UR - https://www.scopus.com/pages/publications/0028355307

U2 - 10.1016/S0040-4039(00)76777-3

DO - 10.1016/S0040-4039(00)76777-3

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AN - SCOPUS:0028355307

SN - 0040-4039

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SP - 2129

EP - 2132

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 14

ER -

Stereoselective oxidations of a β-methylglycal, anhydrodihydroartemisinin

Abstract

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