A highly diastereoselective total synthesis of (±)-heritonin and (±)-heritol

被引:7
作者
Chavan, Subhash P. [1 ]
Garai, Sumanta [1 ]
Kalkote, Uttam R. [1 ]
机构
[1] Natl Chem Lab, Div Organ Chem, CSIR NCL, Pune 411008, Maharashtra, India
关键词
Friedel-Crafts acylation; Butenolide; Tetralone; Dihydroxylation; Cyclization; EFFICIENT SYNTHESIS; MANGROVE PLANTS; TOXICANTS;
D O I
10.1016/j.tet.2012.07.020
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly diastereoselective synthesis of heritol and heritonin by intramolecular cyclization on a preformed sensitive butenolide functionality is described. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8509 / 8514
页数:6
相关论文
共 19 条
[1]   First enantiospecific synthesis of (+)-β-herbertenol [J].
Chavan, SP ;
Thakkar, M ;
Kharul, RK ;
Pathak, AB ;
Bhosekar, GV ;
Bhadbhade, MM .
TETRAHEDRON, 2005, 61 (15) :3873-3879
[2]   An efficient synthesis of (±)-β-herbertenol by a 1,3-cyclopentadione annelation strategy [J].
Chavan, SP ;
Kharul, RK ;
Kale, RR ;
Khobragade, DA .
TETRAHEDRON, 2003, 59 (15) :2737-2741
[3]   AN EFFICIENT ENTRY INTO BUTENOLIDES - SYNTHESIS OF (+/-) MINTLACTONE [J].
CHAVAN, SP ;
ZUBAIDHA, PK ;
AYYANGAR, NR .
TETRAHEDRON LETTERS, 1992, 33 (32) :4605-4608
[4]   Ceric ammonium nitrate (CAN) mediated azidoalkoxylation of enol ethers and olefins [J].
Chavan, SP ;
Subbarao, YT .
TETRAHEDRON LETTERS, 1999, 40 (27) :5073-5074
[5]   An efficient synthesis of alpha-cuparenone [J].
Chavan, SP ;
Ravindranathan, T ;
Patil, SS ;
Dhondge, VD ;
Dantale, SW .
TETRAHEDRON LETTERS, 1996, 37 (15) :2629-2630
[6]   An efficient and practical total synthesis of (±)-α-cuparenone [J].
Chavan, Subhash P. ;
Dhawane, Abasaheb N. ;
Kalkote, Uttam R. .
SYNTHESIS-STUTTGART, 2007, 24 (24) :3827-3830
[7]   A facile total synthesis of (±)-α-cuparenone employing diallylation and RCM as key steps [J].
Chavan, Subhash P. ;
Dhawane, Abasaheb N. ;
Kalkote, Uttam R. .
TETRAHEDRON LETTERS, 2007, 48 (06) :965-966
[8]   The first enantiospecific synthesis of (-)-heritol: absolute configuration determination [J].
Chavan, Subhash P. ;
Thakkar, Mahesh ;
Kalkote, Uttam R. .
TETRAHEDRON LETTERS, 2007, 48 (04) :643-646
[9]   SELECTIVE OXIDATION OF ALDEHYDES TO CARBOXYLIC-ACIDS WITH SODIUM-CHLORITE HYDROGEN-PEROXIDE [J].
DALCANALE, E ;
MONTANARI, F .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (04) :567-569
[10]   CATALYTIC FRIEDEL-CRAFTS ACYLATION OF AROMATIC-COMPOUNDS [J].
EFFENBERGER, F ;
EPPLE, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1972, 11 (04) :300-+