Asymmetric total synthesis of paecilomycin C through intramolecular nucleophilic ring opening of an epoxide

被引：9

作者：

Chakraborty, Joy ^{[1
]}

Nanda, Samik ^{[1
]}

机构：

[1] Indian Inst Technol Kharagpur, Dept Chem, Kharagpur 721302, W Bengal, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2019年 / 17卷 / 31期

关键词：

RESORCYLIC ACID LACTONES; STEREOSELECTIVE TOTAL-SYNTHESIS; HSP90; ALLYLBORATION; BIOSYNTHESIS; CHEMISTRY; ALDEHYDES; BIOLOGY;

D O I：

10.1039/c9ob01504c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The convergent total synthesis of naturally occurring paecilomycin C is described here for the first time. Asymmetric Brown allylation, E-selective cross metathesis, and a biomimetic carboxylate assisted intramolecular nucleophilic ring opening of an epoxide were employed to access the enantiopure gamma-lactone framework of the natural product. Late stage E-selective Julia-Kocienski olefination was then employed to furnish the natural product in an efficient way.

引用

页码：7369 / 7379

页数：11

共 50 条

[1] Asymmetric total synthesis of paecilomycin E, 10′-epi-paecilomycin E and 6′-epi-cochliomycin C
Pal, Pratik
Jana, Nandan
Nanda, Samik
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (41) : 8257 - 8274
[2] Total Synthesis of the Nonenolide Xyolide Using a Regioselective Nucleophilic Epoxide Opening Approach
Wadavrao, Sachin B.
Ghogare, Ramesh S.
Narsaiah, A. Venkat
SYNTHESIS-STUTTGART, 2015, 47 (14): : 2129 - 2137
[3] Asymmetric total synthesis of 5′-epi-paecilomycin-F
Jana, Nandan
Nanda, Samik
TETRAHEDRON-ASYMMETRY, 2012, 23 (10) : 802 - 808
[4] A Carbohydrate Approach for the First Total Synthesis of Cochliomycin C: Stereoselective Total Synthesis of Paecilomycin E, Paecilomycin F and 6′-epi-Cochliomycin C
Mahankali, Bakkolla
Srihari, Pabbaraja
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (18) : 3983 - 3993
[5] Selective synthesis of curdlan ω-carboxyamides by Staudinger ylide nucleophilic ring-opening
Liu, Shu
Gao, Chengzhe
Mosquera-Giraldo, Laura I.
Taylor, Lynne S.
Edgar, Kevin J.
CARBOHYDRATE POLYMERS, 2018, 190 : 222 - 231
[6] Asymmetric total synthesis of ent-heliespirones A & C
Huang, Chong
Liu, Bo
CHEMICAL COMMUNICATIONS, 2010, 46 (29) : 5280 - 5282
[7] Total Syntheses of the Resorcylic Acid.Lactones Paecilomycin F and Cochliomycin C Using an Intramolecular Loh-Type α-Allylation Reaction for Macrolide Formation
Ma, Xiang
Bolte, Benoit
Banwell, Martin G.
Willis, Anthony C.
ORGANIC LETTERS, 2016, 18 (17) : 4226 - 4229
[8] First total synthesis of the highly potent antitumor lactones 8-chlorogoniodiol and parvistone A: Exploiting a bioinspired late-stage epoxide ring-opening
Ramesh, Perla
Reddy, Yarram Narasimha
Reddy, Thatikonda Narendar
Srinivasu, Navuluri
TETRAHEDRON-ASYMMETRY, 2017, 28 (02) : 246 - 249
[9] Asymmetric Total Synthesis of (+)-Mannolide C
Ao, Qiaoqiao
Zhang, Hai-Jun
Zheng, Jinbin
Chen, Xiaoming
Zhai, Hongbin
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (39) : 21267 - 21271
[10] Asymmetric total synthesis of paecilomycin F, cochliomycin C, zeaenol, 5-bromo-zeaenol and 3,5-dibromo-zeaenol by Heck coupling and late stage macrolactonization approach
Pal, Pratik
Chakraborty, Joy
Mali, Anita
Nanda, Samik
TETRAHEDRON, 2016, 72 (18) : 2336 - 2348

← 1 2 3 4 5 →