Regioselective Baeyer–Villiger Oxidation of Steroidal Ketones to Lactones Using BF3/H2O2

Alexey I. Ilovaisky; Valentina M. Merkulova; Vera A. Vil'; Elena I. Chernoburova; Marina A. Shchetinina; Sergey D. Loguzov; Andrey S. Dmitrenok; Igor V. Zavarzin; Alexander O. Terent'ev

doi:10.1002/ejoc.201901701

journal article Jan 07, 2020

Regioselective Baeyer–Villiger Oxidation of Steroidal Ketones to Lactones Using BF3/H2O2

Alexey I. Ilovaisky Valentina M. Merkulova Vera A. Vil' Elena I. Chernoburova Marina A. Shchetinina Sergey D. Loguzov Andrey S. Dmitrenok Igor V. Zavarzin

Alexander O. Terent'ev

European Journal of Organic Chemistry Vol. 2020 No. 3 pp. 402-405 · Wiley

View at Publisher Save 10.1002/ejoc.201901701

Abstract

A regioselective Baeyer–Villiger oxidation of estrone and androstane derivatives into 17a‐oxa‐D‐homosteroids was developed. An important feature of this reaction lies in the selective formation of oxidation products in moderate to high yields using BF3·Et2O/ H2O2 system traditionally applied for peroxide synthesis.

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References

70

[1]

10.1016/j.jsbmb.2013.05.011

[2]

10.1016/j.jsbmb.2011.07.001

[3]

10.1007/s11030-016-9659-x

[4]

10.1021/jm050129p

[5]

10.1016/j.ejmech.2015.08.010

[6]

10.1016/j.steroids.2008.02.006

[7]

10.1016/j.steroids.2004.10.005

[8]

10.1016/j.steroids.2009.07.007

[9]

10.1007/s11224-012-9986-1

[10]

10.1007/s11224-016-0815-9

[11]

10.3762/bjoc.12.162

[12]

Jacobsen R. P. J. Biol. Chem (1947) 10.1016/s0021-9258(17)41106-9

[13]

Levi H. J. Biol. Chem (1947) 10.1016/s0021-9258(17)41107-0

[14]

10.1002/hlca.6602801229

[15]

10.1016/s0040-4020(01)92749-8

[16]

10.1016/s0040-4020(98)00757-1

[17]

10.1016/0039-128x(95)00233-g

[18]

Phytosterols as precursors for the synthesis of aromatase inhibitors: Hemisynthesis of testololactone and testolactone

Shabir H. Lone, Khursheed A. Bhat

Steroids 10.1016/j.steroids.2015.02.011

[19]

10.1002/cber.19881210105

[20]

10.1021/jo00214a016

[21]

10.1021/ja01631a058

[22]

10.1016/j.steroids.2011.06.014

[23]

10.1016/0039-128x(90)90059-k

[24]

10.1016/s0031-9422(98)00286-6

[25]

10.1135/cccc19981646

[26]

Goswami P. Indian J. Chem. Sect. B: Org. Chem. Incl. Med. Chem (2004)

[27]

10.1055/s-1977-24429

[28]

10.1016/s0040-4039(00)60823-7

[29]

10.1002/anie.201204286

[30]

10.1002/ange.201204286

[31]

10.1039/a705601j

[32]

10.1016/j.bmc.2006.05.022

[33]

10.1021/jo0347011

[34]

10.1021/jo00344a035

[35]

10.1135/cccc2011008

[36]

10.1016/j.steroids.2016.03.018

[37]

10.3184/174751917x15064232103083

[38]

10.1016/j.phytochem.2015.09.003

[39]

10.1016/j.jsbmb.2009.12.003

[40]

10.1016/j.steroids.2008.07.008

[41]

10.1016/j.tet.2013.11.039

[42]

10.1016/j.steroids.2009.05.007

[43]

10.3390/molecules181113812

[44]

10.1016/j.steroids.2006.06.005

[45]

10.1016/j.steroids.2004.11.011

[46]

10.1016/j.tet.2012.10.047

[47]

10.1016/j.bbalip.2011.01.005

[48]

10.1016/j.steroids.2014.01.006

[49]

10.1021/jacs.6b12246

[50]

10.1016/s0040-4039(03)01844-6

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Details

Published: Jan 07, 2020
Vol/Issue: 2020(3)
Pages: 402-405
License: View

Authors

A

Alexey I. Ilovaisky

N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences 47 Leninsky Prospect 119991 Moscow Russian Federation; All‐Russian Research Institute for Phytopathology 143050 Moscow Russian Federation

V

Valentina M. Merkulova