Efficient oxidation of oleanolic acid derivatives using magnesium bis(monoperoxyphthalate) hexahydrate (MMPP)

Jorge A. R. Salvador; Vânia M. Moreira; Rui M. A. Pinto; Ana S. Leal; José A. Paixão

doi:10.3762/bjoc.8.17

Efficient oxidation of oleanolic acid derivatives using magnesium bis(monoperoxyphthalate) hexahydrate (MMPP)

Jorge A. R. Salvador, Vânia M. Moreira, Rui M. A. Pinto, Ana S. Leal, José A. Paixão

Strathclyde Institute Of Pharmacy And Biomedical Sciences

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

8 Citations (Scopus)

Abstract

A new, straightforward and high yielding procedure to convert oleanolic acid derivatives into the corresponding δ-hydroxy-γ-lactones, by using the convenient oxidizing agent magnesium bis(monoperoxyphthalate) hexahydrate (MMPP) in refluxing acetonitrile, is reported. In addition, a two-step procedure for the preparation of oleanolic 12-oxo-28-carboxylic acid derivatives directly from Δ12-oleananes, without the need for an intermediary work-up, and keeping the same reaction solvent in both steps, is described as applied to the synthesis of 3,12-dioxoolean-28-oic acid.

Original language	English
Pages (from-to)	164-169
Number of pages	6
Journal	Beilstein Journal of Organic Chemistry
Volume	8
DOIs	https://doi.org/10.3762/bjoc.8.17
Publication status	Published - 30 Jan 2012

Keywords

triterpenoid
oleanolic acid
bismuth(III) triflate

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10.3762/bjoc.8.17

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title = "Efficient oxidation of oleanolic acid derivatives using magnesium bis(monoperoxyphthalate) hexahydrate (MMPP)",

abstract = "A new, straightforward and high yielding procedure to convert oleanolic acid derivatives into the corresponding δ-hydroxy-γ-lactones, by using the convenient oxidizing agent magnesium bis(monoperoxyphthalate) hexahydrate (MMPP) in refluxing acetonitrile, is reported. In addition, a two-step procedure for the preparation of oleanolic 12-oxo-28-carboxylic acid derivatives directly from Δ12-oleananes, without the need for an intermediary work-up, and keeping the same reaction solvent in both steps, is described as applied to the synthesis of 3,12-dioxoolean-28-oic acid.",

keywords = "triterpenoid, oleanolic acid, bismuth(III) triflate",

author = "Salvador, {Jorge A. R.} and Moreira, {V{\^a}nia M.} and Pinto, {Rui M. A.} and Leal, {Ana S.} and Paix{\~a}o, {Jos{\'e} A.}",

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doi = "10.3762/bjoc.8.17",

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T1 - Efficient oxidation of oleanolic acid derivatives using magnesium bis(monoperoxyphthalate) hexahydrate (MMPP)

AU - Salvador, Jorge A. R.

AU - Moreira, Vânia M.

AU - Pinto, Rui M. A.

AU - Leal, Ana S.

AU - Paixão, José A.

PY - 2012/1/30

Y1 - 2012/1/30

N2 - A new, straightforward and high yielding procedure to convert oleanolic acid derivatives into the corresponding δ-hydroxy-γ-lactones, by using the convenient oxidizing agent magnesium bis(monoperoxyphthalate) hexahydrate (MMPP) in refluxing acetonitrile, is reported. In addition, a two-step procedure for the preparation of oleanolic 12-oxo-28-carboxylic acid derivatives directly from Δ12-oleananes, without the need for an intermediary work-up, and keeping the same reaction solvent in both steps, is described as applied to the synthesis of 3,12-dioxoolean-28-oic acid.

AB - A new, straightforward and high yielding procedure to convert oleanolic acid derivatives into the corresponding δ-hydroxy-γ-lactones, by using the convenient oxidizing agent magnesium bis(monoperoxyphthalate) hexahydrate (MMPP) in refluxing acetonitrile, is reported. In addition, a two-step procedure for the preparation of oleanolic 12-oxo-28-carboxylic acid derivatives directly from Δ12-oleananes, without the need for an intermediary work-up, and keeping the same reaction solvent in both steps, is described as applied to the synthesis of 3,12-dioxoolean-28-oic acid.

KW - triterpenoid

KW - oleanolic acid

KW - bismuth(III) triflate

UR - http://www.beilstein-journals.org/bjoc/articles/8/17

U2 - 10.3762/bjoc.8.17

DO - 10.3762/bjoc.8.17

M3 - Article

SN - 1860-5397

VL - 8

SP - 164

EP - 169

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

Efficient oxidation of oleanolic acid derivatives using magnesium bis(monoperoxyphthalate) hexahydrate (MMPP)

Abstract

Keywords

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