Enantiospecific bromonium ion generation and intramolecular capture: a model system for asymmetric bromonium ion-induced polyene cyclisations

被引：14

作者：

Braddock, D. Christopher ^{[1
]}

Marklew, Jared S. ^{[1
]}

Thomas, Alexander J. F. ^{[2
]}

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

[2] Arrow Therapeut Ltd, London SE1 1DB, England

来源：

CHEMICAL COMMUNICATIONS | 2011年 / 47卷 / 32期

基金：

英国工程与自然科学研究理事会;

关键词：

MARINE NATURAL-PRODUCTS; BIOMIMETIC TOTAL-SYNTHESIS; BIOGENETIC-TYPE SYNTHESIS; BROMINATIVE CYCLIZATION; (&/-)-APLYSIN-20; (-)-APLYSISTATIN; HALOCYCLIZATION; BROMOHYDRINS; METABOLITES; APLYSIN-20;

D O I：

10.1039/c1cc13619d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Scalemic bromonium ions generated enantiospecifically by the action of catalytic triflic acid on scalemic regioisomeric bromohydrin derivatives are trapped intramolecularly, enantio-specifically and regioselectively to give bicyclic brominated carbocycles in excellent yield and high enantiomeric excess. This enantiospecific pathway is not significantly perturbed by the addition of a trisubstituted alkene.

引用

页码：9051 / 9053

页数：3

共 53 条

[1] Intramolecular Bromonium Ion Assisted Epoxide Ring-Opening: Capture of the Oxonium Ion with an Added External Nucleophile [J].

Bonney, Karl J. ;

Braddock, D. Christopher ;

White, Andrew J. P. ;

Yaqoob, Muhammad .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (01) :97-104

[2] The generation and trapping of enantiopure bromonium ions [J].

Braddock, D. Christopher ;

Hermitage, Stephen A. ;

Kwok, Lilian ;

Pouwer, Rebecca ;

Redmond, Joanna M. ;

White, Andrew J. P. .

CHEMICAL COMMUNICATIONS, 2009, (09) :1082-1084

[3] Asymmetric Dihydroxylations of 1-Substituted (E)- and (Z)-3-Methylpent-2-en-4-ynes: Full Compliance with the Sharpless Mnemonic Re-established and Embellished [J].

Burghart-Stoll, Heike ;

Boehnke, Oliver ;

Brueckner, Reinhard .

ORGANIC LETTERS, 2011, 13 (05) :1020-1023

[4] Mechanistic considerations of halogenating enzymes [J].

Butler, Alison ;

Sandy, Moriah .

NATURE, 2009, 460 (7257) :848-854

[5] Vanadium bromoperoxidase-catalyzed biosynthesis of halogenated marine natural products [J].

Carter-Franklin, JN ;

Butler, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15060-15066

[6]

Constantino V, 2009, BIOORGAN MED CHEM, V17, P7542

[7] A SHORT AND CONVERGENT ENANTIOSELECTIVE SYNTHESIS OF (3S)-2,3-OXIDOSQUALENE [J].

COREY, EJ ;

NOE, MC ;

SHIEH, WC .

TETRAHEDRON LETTERS, 1993, 34 (38) :5995-5998

[8] ROTALIN A AND B, 2 NOVEL DITERPENE METABOLITES FROM THE ENCRUSTING MEDITERRANEAN SPONGE MYCALE-ROTALIS (BOWERBANK) [J].

CORRIERO, G ;

MADAIO, A ;

MAYOL, L ;

PICCIALLI, V ;

SICA, D .

TETRAHEDRON, 1989, 45 (01) :277-288

[9] Novel stereocontrolled approach to syn- and anti- oxepene-cyclogeranyl trans-fused polycyclic systems:: Asymmetric total synthesis of (-)-aplysistatin, (+)-palisadin A, (+)-palisadin B, (+)-12-hydroxy-palisadin B, and the AB ring system of adociasulfate-2 and toxicol A [J].

Couladouros, EA ;

Vidali, VP .

CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (15) :3822-3835

[10] On the Absolute Configurational Stability of Bromonium and Chloronium Ions [J].

Denmark, Scott E. ;

Burk, Matthew T. ;

Hoover, Andrew J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (04) :1232-+

← 1 2 3 4 5 6 →