Enantioselective Total Synthesis of (-)-Cyathin B2: A Desymmetric Double-Allylboration Approach

被引：1

作者：

Wang, Jianping ^{[1
]}

Yin, Jiacheng ^{[1
]}

Imtiaz, Hayatullah ^{[1
]}

Wang, Hongyu ^{[1
]}

Li, Yun ^{[1
]}

机构：

[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2024年 / 146卷 / 36期

基金：

中国国家自然科学基金;

关键词：

CYATHANE DITERPENOIDS; CLEMMENSEN REDUCTION; KETONES; CONVERSION; DIBORATION; METHYLENE; REAGENTS; DISCOVERY; ALDEHYDES; OLEFINS;

D O I：

10.1021/jacs.4c08042

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A powerful Pt-catalyzed asymmetric diboration/desymmetric double-allylboration cascade reaction has been developed for the construction of synthetically useful, densely functionalized hydrindanes with five stereocenters, including three quaternary ones, in good yields and excellent enantiomeric excess (ee) values within a single synthetic operation. A unified strategy utilizing this key tandem methodology enabled the concise asymmetric total synthesis of cyathane diterpene (-)-Cyathin B-2 in 14 steps from commercially available starting materials, thereby demonstrating its remarkable potential in the synthesis of hydrindane-containing natural products and pharmaceuticals.

引用

页码：25078 / 25087

页数：10

共 50 条

[1] Enantioselective total synthesis of (−)-cyathin B2
Yu Kobayakawa
Masahisa Nakada
The Journal of Antibiotics, 2014, 67 : 483 - 485
[2] Enantioselective total synthesis of (-)-cyathin B2
Kobayakawa, Yu
Nakada, Masahisa
JOURNAL OF ANTIBIOTICS, 2014, 67 (06): : 483 - 485
[3] Total Synthesis of Cyathin A3 and Cyathin B2
Kim, Keunho
Cha, Jin Kun
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (29) : 5334 - 5336
[4] Enantioselective total synthesis of cyathin A3
Ward, Dale E.
Shen, Jianheng
ORGANIC LETTERS, 2007, 9 (15) : 2843 - 2846
[5] Synthetic studies on cyathins:: Enantioselective total synthesis of (+)-allocyathin B2
Takano, M
Umino, A
Nakada, M
ORGANIC LETTERS, 2004, 6 (26) : 4897 - 4900
[6] A general approach to cyathin diterpenes.: Total synthesis of allocyathin B3
Ward, DE
Gai, YZ
Qiao, Q
ORGANIC LETTERS, 2000, 2 (14) : 2125 - 2127
[7] Total Synthesis of Vineomycin B2
Kusumi, Shunichi
Tomono, Satoshi
Okuzawa, Shunsuke
Kaneko, Erika
Ueda, Takashi
Sasaki, Kaname
Takahashi, Daisuke
Toshima, Kazunobu
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (42) : 15909 - 15912
[8] Total synthesis of vineomycin B2
Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan
Toshima, K. (toshima@applc.keio.ac.jp), 1600, American Chemical Society (135):
[9] Total synthesis of topsentolide B2
Fernandes, Rodney A.
Kattanguru, Pullaiah
TETRAHEDRON LETTERS, 2011, 52 (15) : 1788 - 1790
[10] TOTAL SYNTHESIS OF THROMBOXANE B2
NELSON, NA
JACKSON, RW
TETRAHEDRON LETTERS, 1976, (37) : 3275 - 3278

← 1 2 3 4 5 →