Total synthesis of chrysamide B

被引：9

作者：

Berube, Christopher ^{[1
]}

Carpentier, Claudia ^{[1
]}

Voyer, Normand ^{[1
]}

机构：

[1] Univ Laval, PROTEO, Dept Chim, Fac Sci & Genie, 1045 Ave Med, Quebec City, PQ G1V 0A6, Canada

来源：

TETRAHEDRON LETTERS | 2017年 / 58卷 / 24期

基金：

加拿大自然科学与工程研究理事会;

关键词：

Chrysamide; Chiral piperazines; Nitro natural products; Chiral epoxides; Natural product synthesis; POLYMER-BOUND OXIME; ASYMMETRIC EPOXIDATION; DRAGMACIDIN-B; A-C; PIPERAZINE; DERIVATIVES; OXIDATION; PEPTIDES; ANALOGS;

D O I：

10.1016/j.tetlet.2017.04.079

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report an efficient synthesis of the dimeric trans-epoxyamide chrysamide B, recently isolated from the deep-sea-derived fungus Penicillium chrysogenum SCSI041001. Our synthetic strategy exploits a convergent approach using solid,phase peptide synthesis for the piperazine core and a Sharpless-Katsuki epoxidation to prepare the chiral epoxyacid. The double amidation final step provides chrysamide B that was thoroughly characterized with all spectra identical to those of the natural sample. The approach was devised to facilitate the preparation of a library of analogs of chrysamide B. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：2334 / 2336

页数：3

共 50 条

[1] Total Synthesis of Plakortone B
Xie, Xin-Gang
Wu, Xun-Wei
Lee, Hing-Ken
Peng, Xiao-Shui
Wong, Henry N. C.
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (23) : 6933 - 6941
[2] Total Synthesis of Phyllanemblinin B
Matsumoto, Shintaro
Wakamori, Shinnosuke
Nishii, Kentaro
Tanaka, Takashi
Yamada, Hidetoshi
SYNLETT, 2020, 31 (14) : 1389 - 1393
[3] A Total Synthesis of (-)-Nardoaristolone B
Ople, Rohini S.
Handore, Kishor L.
Kamat, Nidhi S.
Reddy, D. Srinivasa
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (22) : 3804 - 3808
[4] Total Synthesis of Dehydroaltenuene A. Revision of the Structure and Total Synthesis of Dihydroaltenuene B
Altemoeller, Martina
Podlech, Joachim
JOURNAL OF NATURAL PRODUCTS, 2009, 72 (07): : 1288 - 1290
[5] Total Synthesis of (+)-Schweinfurthins B and E
Topczewski, Joseph J.
Neighbors, Jeffrey D.
Wiemer, David F.
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (18) : 6965 - 6972
[6] Asymmetric total synthesis of (+)-propolisbenzofuran B
Sen, Biswajit
Bera, Mainak
Singh, Maya Shankar
Hajra, Saumen
CHEMICAL COMMUNICATIONS, 2023, 59 (53) : 8254 - 8257
[7] Novel total synthesis of anserinone A and B
Whisenant, Jonathan
Vinson, Daniel
Blanco, Michael
Hughes, Carson
David, Samuel
SYNTHETIC COMMUNICATIONS, 2017, 47 (04) : 268 - 272
[8] Iterative Iodocyclization: Total Synthesis of Polyrhacitide B
Mohapatra, Debendra K.
Krishnarao, P. Sivarama
Bhimireddy, Eswar
Yadav, Jhillu S.
SYNTHESIS-STUTTGART, 2014, 46 (12): : 1639 - 1647
[9] A Highly Convergent Total Synthesis of Norhalichondrin B
Nicolaou, K. C.
Pan, Saiyong
Shelke, Yogesh
Ye, Qiuji
Das, Dipendu
Rigol, Stephan
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (49) : 20970 - 20979
[10] Total Synthesis of the Marine Ladder Polyether Gymnocin B
Sittihan, Satapanawat
Jamison, Timothy F.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (28) : 11239 - 11244

← 1 2 3 4 5 →