Total Synthesis of (-)-Bacchopetiolone via an Asymmetric Hydroxylative Phenol Dearomatization/[4+2]-Dimerization Cascade Promoted by a Novel Salen-Type Chiral lodane

被引：42

作者：

Coffinier, Romain ^{[1
]}

El Assal, Mourad ^{[1
]}

Peixoto, Philippe A. ^{[1
]}

Bosset, Cyril ^{[1
]}

Miqueu, Karinne ^{[2
]}

Sotiropoulos, Jean-Marc ^{[2
]}

Pouysegu, Laurent ^{[1
]}

Quideau, Stephane ^{[1
]}

机构：

[1] Univ Bordeaux, ISM CNRS UMR 5255, 351 Cours Liberat, F-33405 Talence, France

[2] Univ Pau & Pays Adour, IPREM CNRS UMR 5254, Helioparc,2 Ave Pierre Angot, F-64053 Pau 09, France

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 05期

关键词：

HYPERVALENT IODINE REAGENTS; OXIDATIVE DEAROMATIZATION; ORTHOQUINONE MONOKETALS; SIBX; REACTIVITY; ACCESS;

D O I：

10.1021/acs.orglett.6b00224

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total and biomimetic synthesis of the natural bis(sesquiterpene) (-)-bacchopetiolone (revised structure) was completed through a highly diastereoselective hydroxylative phenol dearomatization/[4+2]-dimerization cascade conversion of (+)-curcuphenol using a novel C-2-symmetrical chiral Salen-type bis(lambda(5)-iodane).

引用

页码：1120 / 1123

页数：4

共 45 条

[1] Exceedingly Efficient Synthesis of (±)-Grandifloracin and Acylated Analogues [J].

Bergner, Magnus ;

Duquette, Douglas C. ;

Chio, Linda ;

Stoltz, Brian M. .

ORGANIC LETTERS, 2015, 17 (12) :3008-3010

[2] Reagent and Catalyst Design for Asymmetric Hypervalent Iodine Oxidations [J].

Berthiol, Florian .

SYNTHESIS-STUTTGART, 2015, 47 (05) :587-603

[3] Progress toward the total synthesis of bacchopetiolone:: Application of a tandem aromatic oxidation/Diels-Alder reaction [J].

Berube, Amelie ;

Drutu, Ioana ;

Wood, John L. .

ORGANIC LETTERS, 2006, 8 (24) :5421-5424

[4] Asymmetric Oxidation of o-Alkylphenols with Chiral 2-(o-Iodoxyphenyl)-oxazolines [J].

Boppisetti, Jagadish K. ;

Birman, Vladimir B. .

ORGANIC LETTERS, 2009, 11 (06) :1221-1223

[5] Asymmetric Hydroxylative Phenol Dearomatization Promoted by Chiral Binaphthylic and Biphenylic Iodanes [J].

Bosset, Cyril ;

Coffinier, Romain ;

Peixoto, Philippe A. ;

El Assal, Mourad ;

Miqueu, Karinne ;

Sotiropoulos, Jean-Marc ;

Pouysegu, Laurent ;

Quideau, Stephane .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (37) :9860-9864

[6] Diastereoselective IBX Oxidative Dearomatization of Phenols by Remote Induction: Towards the Epicocconone Core Framework [J].

Boulange, Agathe ;

Peixoto, Philippe A. ;

Franck, Xavier .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (37) :10241-10245

[7]

Ding Q., 2012, Synthesis, V45, P1

[8] Asymmetric Dearomatizing Spirolactonization of Naphthols Catalyzed by Spirobiindane-Based Chiral Hypervalent Iodine Species [J].

Dohi, Toshifumi ;

Takenaga, Naoko ;

Nakae, Tomofumi ;

Toyoda, Yosuke ;

Yamasaki, Mikio ;

Shiro, Motoo ;

Fujioka, Hiromichi ;

Maruyama, Akinobu ;

Kita, Yasuyuki .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (11) :4558-4566

[9] Enantioselective synthesis of bicyclo[2.2.2]octenones using a copper-mediated oxidative dearomatization/[4+2] dimerization cascade [J].

Dong, Suwei ;

Zhu, Jianglong ;

Porco, John A., Jr. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (09) :2738-+

[10] Facile Syntheses of (±)-Curcuphenol, (±)-Curcudiol, (±)-Curcuhydroquinone, and (±)-Curcuquinone [J].

Du, Zhenting ;

Li, Yong ;

Wang, Yin ;

Ding, Lichun ;

Gao, Jinming .

SYNTHETIC COMMUNICATIONS, 2010, 40 (13) :1920-1926

← 1 2 3 4 5 →