Regioselective Reactions of Highly Substituted Arynes

被引:112
作者
Tadross, Pamela M. [1 ]
Gilmore, Christopher D. [1 ]
Bugga, Pradeep [1 ]
Virgil, Scott C. [1 ]
Stoltz, Brian M. [1 ]
机构
[1] CALTECH, Div Chem & Chem Engn, Arnold & Mabel Beckman Labs Chem Synth, Pasadena, CA 91125 USA
关键词
REACTIVITY; ORIENTATION; ANNULATION; ACCESS; ACID;
D O I
10.1021/ol1000796
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The fully regioselective reactivity of four new highly substituted silyl aryl triflate aryne precursors In aryne acyl-alkylation, acyl-alkylation/condensation, and heteroannulation reactions Is reported. The application of these more complex arynes provides access to diverse natural product scaffolds and obviates late-stage functionalization of aromatic rings.
引用
收藏
页码:1224 / 1227
页数:4
相关论文
共 24 条
[1]   Multi-functionalization of gallic acid towards improved synthesis of α- and β-DDB [J].
Alam, A ;
Takaguchi, Y ;
Ito, H ;
Yoshida, T ;
Tsuboi, S .
TETRAHEDRON, 2005, 61 (07) :1909-1918
[2]   Expedient synthesis of 3-hydroxyisoquinolines and 2-hydroxy-1,4-naphthoquinones via one-pot aryne acyl-alkylation/condensation [J].
Allan, Kevin M. ;
Hong, Boram D. ;
Stoltz, Brian M. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (23) :4960-4964
[3]   A Concise Total Synthesis of (-)-Quinocarcin via Aryne Annulation [J].
Allan, Kevin M. ;
Stoltz, Brian M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (51) :17270-+
[4]   SCREENING OF GENUS CERCOSPORA FOR SECONDARY METABOLITES [J].
ASSANTE, G ;
LOCCI, R ;
CAMARDA, L ;
MERLINI, L ;
NASINI, G .
PHYTOCHEMISTRY, 1977, 16 (02) :243-247
[5]   SYNTHESIS OF 3-HYDROXYISOQUINOLINES AND 2-HYDROXY-1-4-NAPHTHAQUINONES FROM ESTERS OF 2-ACYL-4-5-DIMETHOXYPHENYLACETIC ACIDS [J].
BENTLEY, HR ;
DAWSON, W ;
SPRING, FS .
JOURNAL OF THE CHEMICAL SOCIETY, 1952, (MAY) :1763-1768
[6]   ORIENTATION AND REACTIVITY IN NUCLEOPHILIC ADDITION TO ARYNES POSSESSING CHARGED SUBSTITUENTS .I. ORIENTATION AND REACTIVITY IN NUCLEOPHILIC ADDITION TO BENZYNE-3- AND -4-CARBOXYLATE [J].
BIEHL, ER ;
NIEH, E ;
LI, HM ;
HONG, CI .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (03) :500-&
[7]   SUBSTITUENT EFFECTS ON REACTIVITY OF ARYNES . PRODUCT DISTRIBUTIONS AS AN INDEX OF RELATIVE REACTIVITIES OF ARYNES IN METHYLAMINE AND DIMETHYLAMINE SOLVENTS [J].
BIEHL, ER ;
NIEH, E ;
HSU, KC .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (11) :3595-&
[8]   Efficient Synthesis of 2-(Trimethylsilyl)phenyl Trifluoromethanesulfonate: A Versatile Precursor to o-Benzyne [J].
Bronner, Sarah M. ;
Garg, Neil K. .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (22) :8842-8843
[9]   ORIENTATION REACTIVITY AND MECHANISM IN ADDITION OF METHANOL TO 4-CHLOROBENZYNE [J].
BUNNETT, JF ;
HAPPER, DAR ;
PATSCH, M ;
PYUN, C ;
TAKAYAMA, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (22) :5250-&
[10]   Indolyne and Aryne Distortions and Nucleophilic Regioselectivites [J].
Cheong, Paul H. -Y. ;
Paton, Robert S. ;
Bronner, Sarah M. ;
Im, G-Yoon J. ;
Garg, Neil K. ;
Houk, K. N. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (04) :1267-+