Studies towards the Total Synthesis of Kadcotrione B

被引:3
作者
Reddy, Julakanti Satyanarayana [1 ]
Gangababu, Marri [1 ]
Manimala, Patel [1 ]
Rammohan, Aluru [1 ,2 ]
Yadav, Jillu Singh [1 ]
机构
[1] CSIR Indian Inst Chem Technol, Div Nat Prod Chem, Hyderabad 500007, Telangana, India
[2] Sri Venkateswara Univ, Dept Chem, Tirupati 517502, Andhra Pradesh, India
来源
SYNTHESIS-STUTTGART | 2020年 / 52卷 / 05期
关键词
aldol condensation; diastereoselectivity; Hagiwara-Weiland-Miescher ketone; Horner-Wadsworth-Emmons reaction; Kadcotrione; Michael addition; ENANTIOSELECTIVE SYNTHESIS; ABSOLUTE-CONFIGURATION; SCHISANDRA; ACID; TRITERPENOIDS; CYCLIZATION; OXIDATION; LIBRARY; STEREO; FAMILY;
D O I
10.1055/s-0039-1691494
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convergent and efficient approach towards the total synthesis of Kadcotrione B is described. For this purpose, the syntheses of two fragments, 6/6/5-fused tricyclic ring and C-9 side chain, were accomplished. The salient features of these syntheses are the utilization of aldol condensation, Evans aldol reaction, Horner-Wadsworth-Emmons olefination, Michael addition, Robinson annulation, and Wacker oxidation.
引用
收藏
页码:735 / 743
页数:9
相关论文
共 50 条
[11]   Asymmetric total synthesis of (+)-ovafolinins A and B [J].
Fang, Xianhe ;
Shen, Lei ;
Hu, Xiangdong .
CHEMICAL COMMUNICATIONS, 2018, 54 (54) :7539-7541
[12]   Stereoselective Total Synthesis of (±)-Pleurospiroketals A and B [J].
Thorat, Sagar S. ;
Krishna, Gamidi Rama ;
Kontham, Ravindar .
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (19) :13572-13582
[13]   Studies towards the synthesis of aculeatin C [J].
Peuchmaur, Marine ;
Wong, Yung-Sing .
SYNLETT, 2007, (18) :2902-2906
[14]   Olefin Cross-Metathesis: Studies towards the Total Synthesis of (+)-Bitungolide F [J].
Dayaker, Gandrath ;
Krishna, Palakodety Radha .
HELVETICA CHIMICA ACTA, 2014, 97 (06) :868-880
[15]   Further studies of an approach to a total synthesis of phomactins [J].
Blackburn, Timothy J. ;
Helliwell, Madeleine ;
Kilner, Michael J. ;
Lee, Alan T. L. ;
Thomas, Eric J. .
TETRAHEDRON LETTERS, 2009, 50 (26) :3550-3554
[16]   Stereoselective total synthesis of pachastrissamine (jaspine B) [J].
Passiniemi, Mikko ;
Koskinen, Ari M. P. .
TETRAHEDRON LETTERS, 2008, 49 (06) :980-983
[17]   Total Synthesis and Structural Revision of (+)-Yaoshanenolide B [J].
Kotzabasaki, Vasiliki ;
Vassilikogiannakis, Georgios ;
Stratakis, Manolis .
ORGANIC LETTERS, 2016, 18 (19) :4982-4985
[18]   Studies on the Total Synthesis of Lactonamycin: Synthesis of the Fused Pentacyclic B-F Ring Unit [J].
Jacques, Sylvain A. ;
Michaelis, Simon ;
Gebhardt, Bjoern ;
Blum, Andreas ;
Lebrasseur, Nathalie ;
Larrosa, Igor ;
White, Andrew J. P. ;
Barrett, Anthony G. M. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (01) :107-113
[19]   Studies directed towards the total synthesis of narbonolide: stereoselective synthesis of the C1-C15 chain [J].
Yadav, Jhillu S. ;
Kavita, Aala ;
Rao, Kovvuri V. Raghavendra ;
Mohapatra, Debendra K. .
TETRAHEDRON LETTERS, 2013, 54 (26) :3329-3331
[20]   Total Synthesis and Structural Revision of the Cytotoxin Aruncin B [J].
Ribaucourt, Aubert ;
Hodgson, David M. .
ORGANIC LETTERS, 2016, 18 (17) :4364-4367