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
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
[21]   Total synthesis of the marine natural product (-)-clavosolide A. A showcase for the Petasis-Ferrier union/rearrangement tactic [J].
Smith, Amos B., III ;
Simov, Vladimir .
ORGANIC LETTERS, 2006, 8 (15) :3315-3318
[22]   Total synthesis, structural revision, and absolute configuration of (+)-clavosolide A [J].
Son, JB ;
Kim, SN ;
Kim, NY ;
Lee, DH .
ORGANIC LETTERS, 2006, 8 (04) :661-664
[23]   Enantioselective Total Synthesis of (-)-Clavosolide A and B [J].
Son, Jung Beom ;
Kim, Si Nae ;
Kim, Na Yeong ;
Hwang, Min-ho ;
Lee, Wonsun ;
Lee, Duck Hyung .
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2010, 31 (03) :653-663
[24]   Biomimetic total synthesis of (-)-Erinacine E [J].
Watanabe, Hideaki ;
Nakada, Masahisa .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (04) :1150-+
[25]   Stereoselective synthesis of (+)-cryptocarya diacetate by an iterative Prins cyclisation and reductive cleavage sequence [J].
Yadav, J. S. ;
Rao, P. Purushothama ;
Reddy, M. Sridhar ;
Rao, N. Venkateswar ;
Prasad, A. R. .
TETRAHEDRON LETTERS, 2007, 48 (08) :1469-1471