Total synthesis of clavosolide A via tandem allylic oxidation/oxa-conjugate addition reaction

被引：7
作者：
Baker, Joseph B. [1 ]
Kim, Hyoungsu [2 ]
Hong, Jiyong [1 ]
机构：
[1] Duke Univ, Dept Chem, Durham, NC 27708 USA
[2] Ajou Univ, Coll Pharm, Suwon 443749, South Korea
来源：
TETRAHEDRON LETTERS | 2015年 / 56卷 / 23期
关键词：
Clavosolide; Total synthesis; Tandem reaction; Oxa-conjugate addition; gem-Disubstituent effect; Tetrahydropyran; NATURAL-PRODUCT (-)-CLAVOSOLIDE-A; STEREOSELECTIVE-SYNTHESIS; ABSOLUTE-CONFIGURATION; BENZOIC ANHYDRIDE; FORMAL SYNTHESIS; LACTONES; ESTERS;
D O I：
10.1016/j.tetlet.2014.11.135
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The tandem allylic oxidation/oxa-conjugate addition reaction promoted by the gem-disubstituent effect in conjunction with the NHC-mediated oxidative esterification was explored for the facile synthesis of clavosolide A. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3120 / 3122
页数：3
相关论文
共 25 条
[1]   Total synthesis of the marine natural product (-)-clavosolide A [J].
Barry, Conor S. ;
Elsworth, Jon D. ;
Seden, Peter T. ;
Bushby, Nick ;
Harding, John R. ;
Alder, Roger W. ;
Willis, Christine L. .
ORGANIC LETTERS, 2006, 8 (15) :3319-3322
[2]   Total synthesis of a diastereomer of the marine natural product clavosolide A [J].
Barry, CS ;
Bushby, N ;
Charmant, JPH ;
Elsworth, JD ;
Harding, JR ;
Willis, CL .
CHEMICAL COMMUNICATIONS, 2005, (40) :5097-5099
[3]   Stereoselective Synthesis of 2,6-trans-Tetrahydropyran via Primary Diamine-Catalyzed Oxa-Conjugate Addition Reaction of α,β-Unsaturated Ketone: Total Synthesis of Psymberin [J].
Byeon, Seong Rim ;
Park, Heekwang ;
Kim, Hyoungsu ;
Hong, Jiyong .
ORGANIC LETTERS, 2011, 13 (21) :5816-5819
[4]   An Efficient Formal Synthesis of (-)-Clavosolide A Featuring a "Mismatched" Stereoselective Oxocarbenium Reduction [J].
Carrick, Jesse D. ;
Jennings, Michael P. .
ORGANIC LETTERS, 2009, 11 (03) :769-772
[5]   Studies directed towards the total synthesis of clavosolides: synthesis of an isomer of clavosolide A [J].
Chakraborty, TK ;
Reddy, VR .
TETRAHEDRON LETTERS, 2006, 47 (13) :2099-2102
[6]   Total synthesis of clavosolide A [J].
Chakraborty, Tushar Kanti ;
Reddy, Vakiti Ramkrishna ;
Gajula, Praveen Kumar .
TETRAHEDRON, 2008, 64 (22) :5162-5167
[7]   Total synthesis of (-)-clavosolide A [J].
Chakraborty, Tushar Kanti ;
Reddy, Vakiti Ramkrishna ;
Chattopadhyay, Anut Kumar .
TETRAHEDRON LETTERS, 2006, 47 (42) :7435-7438
[8]   IODINE MONOBROMIDE (IBR) AT LOW-TEMPERATURE - ENHANCED DIASTEREOSELECTIVITY IN ELECTROPHILIC CYCLIZATIONS OF HOMOALLYLIC CARBONATES [J].
DUAN, JJW ;
SMITH, AB .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (14) :3703-3711
[9]   Total Synthesis of Cyanolide A and Confirmation of Its Absolute Configuration [J].
Kim, Hyoungsu ;
Hong, Jiyong .
ORGANIC LETTERS, 2010, 12 (12) :2880-2883
[10]   Stereoselective Synthesis of 2,6-cis-Tetrahydropyrans through a Tandem Allylic Oxidation/Oxa-Michael Reaction Promoted by the gem-Disubstituent Effect: Synthesis of (+)-Neopeltolide Macrolactone [J].
Kim, Hyoungsu ;
Park, Yongho ;
Hong, Jiyong .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (41) :7577-7581
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