Enantioselective Formal Synthesis of the Cytotoxic Topoisomerase II Inhibitor Deoxythysanone, Catalyzed by Chiral Spiroborate Ester

被引：2

作者：

Chopade, M. U. ^{[1
,2
]}

Nikalje, M. D. ^{[2
]}

Patil, H. S. ^{[3
]}

Chopade, A. U. ^{[4
]}

机构：

[1] St Dnyaneshwar Mahavidyalaya, Dept Chem, Aurangabad 431120, Maharashtra, India

[2] Savitribai Phule Univ, Dept Chem, Pune 411007, Maharashtra, India

[3] Moreshwar Coll, Dept Chem, Bhokardan 431114, India

[4] Dahiwadi Coll, Dahiwadi 415508, India

来源：

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 56卷 / 04期

关键词：

homobenzylic ketone; spiroborate esters; asymmetric reduction; alcohol; deoxythysanone; 3C-PROTEASE INHIBITOR; PYRANONAPHTHOQUINONE ANTIBIOTICS; DEOXY ANALOGS; STEREOCHEMISTRY; ELEUTHERIN; REDUCTION; THYSANONE;

D O I：

10.1134/S1070428020040181

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bioactive pyranonaphthoquinone analogs, (1R,3S)-deoxythysanone, (1R,3S)-thysanone, and (1R,3S)-demethoxythysanone can be efficiently synthesized from a common intermediate product, (S)-3-methyl-3,4-dihydro-1H-isochromene-5,8-dione. We have developed a short synthetic route to pyranonaphthoquinone antibiotics, which involves enantioselective reduction of homobenzylic ketone in the presence of a chiral spiroborate catalyst with 87% enantiomeric excess as the key step. The subsequent oxa-Pectet-Spengler reaction, followed by oxidative demethylation, afforded deoxythysanone.

引用

页码：693 / 697

页数：5

共 50 条

[21] Synthesis of chiral primary amines via reduction of oxime ethers with chiral spiroborate ester derived from diphenylvalinol and etylene glycol
Fidalgo, Kiara M. Santiago
Claudio, Valerie E. Torres
Ortiz-Marciales, Margarita
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
[22] Chiral borate esters in asymmetric synthesis - Part 2 - Asymmetric borane reduction of prochiral ketones in the presence of a chiral spiroborate ester
Liu, DJ
Shan, ZX
Zhou, Y
Wu, XJ
Qin, JG
HELVETICA CHIMICA ACTA, 2004, 87 (09) : 2310 - 2317
[23] Synthesis of chiral primary amines via reduction of oxime ethers with chiral spiroborate ester derived from diphenylvalinol and ethylene glycol
Torres-Claudio, Valerie E.
Santiago-Fidalgo, Kiara M.
Espinosa-Diaz, Sandraliz
Alvares-Estrella, Jaime L.
Melendez-Gonzalez, Hector J.
Farre-Rosado, Silvia M.
Ortiz-Marciales, Margarita
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
[24] Rhodium(II)-Catalyzed Enantioselective Synthesis of Troponoids
Murarka, Sandip
Jia, Zhi-Jun
Merten, Christian
Daniliuc, Constantin-G.
Antonchick, Andrey P.
Waldmann, Herbert
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (26) : 7653 - 7656
[25] Synthesis of new chiral oxetanes via enantioselective reduction of prochiral β-halogenated aryl ketones with amino spiroborate esters
Rivera, Javier O.
Roldan, Lilinete
Padilla, Miriam M.
Ortiz-Marciales, Margarita
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
[26] Synthesis of rotenoid derivatives with cytotoxic and topoisomerase II inhibitory activities
Sangthong, Supranee
Krusong, Kuakarun
Ngamrojanavanich, Nattaya
Vilaivan, Tirayut
Puthong, Songchan
Chandchawan, Supajittra
Muangsin, Nongnuj
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (16) : 4813 - 4818
[27] Enantioselective formal synthesis of (-)-ovalicin using quinic acid as a chiral template
Barco, A
Benetti, S
De Risi, C
Marchetti, P
Pollini, GP
Zanirato, V
TETRAHEDRON-ASYMMETRY, 1998, 9 (16) : 2857 - 2864
[28] Synthesis of elenic acid, an inhibitor of Topoisomerase II.
Hsung, RP
Golding, GM
Johnson, EW
Pierson, TW
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U222 - U222
[29] SYNTHESIS OF THE TOPOISOMERASE-II INHIBITOR BE-10988
MOODY, CJ
SWANN, E
TETRAHEDRON LETTERS, 1993, 34 (12) : 1987 - 1988
[30] First synthesis of subelliptenone F, an inhibitor of topoisomerase II
Ohira, S
Fukamachi, N
Nakagawa, O
Yamada, M
Nozaki, H
Iinuma, M
CHEMISTRY LETTERS, 2000, (05) : 464 - 465

← 1 2 3 4 5 →