Divergent Total Syntheses of Illicium Sesquiterpenes through Late-Stage Skeletal Reorganization

被引：9

作者：

Fu, Pengfei ^{[1
]}

Liu, Tao ^{[1
]}

Shen, Yang ^{[1
]}

Lei, Xin ^{[1
]}

Xiao, Tianjie ^{[1
]}

Chen, Peng ^{[1
]}

Qiu, Dongsheng ^{[1
]}

Wang, Zhen ^{[1
]}

Zhang, Yandong ^{[1
]}

机构：

[1] Xiamen Univ, Coll Chem & Chem Engn, State Key Lab Phys Chem Solid Surfaces, Key Lab Chem Biol Fujian Prov,iCHEM, Xiamen 361005, Fujian, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2023年 / 145卷 / 33期

基金：

中国国家自然科学基金;

关键词：

PREZIZAANE-TYPE SESQUITERPENES; NEUROTROPHIC ACTIVITY; ENANTIOSPECIFIC SYNTHESIS; CHEMISTRY; ANALOGS;

D O I：

10.1021/jacs.3c06442

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We disclose unified, protecting-group-free, bioinspireddivergenttotal syntheses of eight allo-cedrane and seco-prezizaane Illicium sesquiterpenesand formal syntheses of five anislactone sesquiterpenes. The efficiencyof our approach derives from rapid access to the 15-carbon tricycliccarboxylic acid through cationic epoxide-ene cyclization and HAT oxygenation,transformation of this intermediate into three distinct tricyclicprecursors via Lewis acid-mediated skeletal reorganizations, subsequentprogrammed oxidation level enhancement, and a biomimetic oxidation-initiatedskeletal rearrangement cascade. Consequently, we created a syntheticcorrelation map of the three most prevalent Illicium sesquiterpene families.

引用

页码：18642 / 18648

页数：7

共 50 条

[21] Biomimetic Syntheses of Analogs of Hongoquercin A and B by Late-Stage Derivatization
Mies, Thomas
White, Andrew J. P.
Parsons, Philip J.
Barrett, Anthony G. M.
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (02): : 1802 - 1817
[22] Late-Stage Functionalization for the Divergent Synthesis of Podophyllotoxin Derivatives by Rhodium Catalysis
Zhao, Yue
Shen, Yangpeng
He, Jian
Li, Jing
Zhou, Shengbin
Wang, Yunbo
Li, Chunpu
Liu, Hong
CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (43)
[23] Late-Stage Functionalization for the Divergent Synthesis of Podophyllotoxin Derivatives by Rhodium Catalysis
Zhao, Yue
Shen, Yangpeng
He, Jian
Li, Jing
Wang, Yunbo
Zhou, Shengbin
Li, Chunpu
Liu, Hong
CHEMISTRY-A EUROPEAN JOURNAL, 2023,
[24] Total synthesis of peshawaraquinone through late-stage [3+2] cycloaddition or α-ketol rearrangement
Guo, Huihui
Ren, Li
Sang, Xueli
Lu, Xuena
Li, Tian
Zhou, Wenming
Rauf, Abdur
Hao, Hong-Dong
ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (04) : 1084 - 1089
[25] Molecular Phenotyping of Late-Stage Knee Osteoarthritis Synovium Through Total RNA-Sequencing
Ratneswaran, Anusha
Pastrello, Chiara
Potla, Pratibha
Espin-Garcia, Osvaldo
Lively, Starlee
Perruccio, Anthony
Rampersaud, Raj
Gandhi, Rajiv
Kapoor, Mohit
ARTHRITIS & RHEUMATOLOGY, 2020, 72
[26] Divergent synthesis of complex withanolides enabled by a scalable route and late-stage functionalization
Che, Wen
Wojitas, Lukasz
Shan, Chuan
Lopchuk, Justin M.
SCIENCE ADVANCES, 2024, 10 (26): : eadp9375
[27] Capitellocondylar total elbow replacement in late-stage rheumatoid arthritis
Ovesen, J
Olsen, BS
Johannsen, HV
Sojbjerg, JE
JOURNAL OF SHOULDER AND ELBOW SURGERY, 2005, 14 (04) : 414 - 420
[28] Total synthesis of LewisX using a late-stage crystalline intermediate
Munneke, Stefan
Painter, Gavin F.
Gainsford, Graeme J.
Stocker, Bridget L.
Timmer, Mattie S. M.
CARBOHYDRATE RESEARCH, 2015, 414 : 1 - 7
[29] Total syntheses of (±)-spiroindimicins B and C enabled by a late-stage Schollkopf-Magnus-Barton-Zard (SMBZ) reaction
Blair, Lachlan M.
Sperry, Jonathan
CHEMICAL COMMUNICATIONS, 2016, 52 (04) : 800 - 802
[30] Late-stage divergent synthesis and antifouling activity of geraniol-butenolide hybrid molecules
Takamura, Hiroyoshi
Ohashi, Takumi
Kikuchi, Takahiro
Endo, Noriyuki
Fukuda, Yuji
Kadota, Isao
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (26) : 5549 - 5555

← 1 2 3 4 5 →