Structural Revision of (+)-Uprolide F Diacetate Confirmed by Asymmetric Total Synthesis

被引：24

作者：

Zhu, Liangyu ^{[1
]}

Tong, Rongbiao ^{[1
]}

机构：

[1] Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Hong Kong, Peoples R China

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 08期

基金：

中国国家自然科学基金;

关键词：

MARINE NATURAL-PRODUCTS; CORAL SARCOPHYTON-CRASSOCAULE; BAYLIS-HILLMAN REACTION; METHYLENE-GAMMA-BUTYROLACTONES; GORGONIAN EUNICEA-MAMMOSA; SOFT CORAL; STEREOSELECTIVE-SYNTHESIS; SINULARIA-FLEXIBILIS; EUPALMERIN ACETATE; UPROLIDE-D;

D O I：

10.1021/acs.orglett.5b00700

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new structure for the cytotoxic cembranolide uprolide F diacetate (UFD) was proposed, and an enantioselective total synthesis was accomplished to confirm that our revised structure correctly represented the natural UFD and its absolute configuration. Our synthesis features a late-stage, highly efficient, and diastereoselective NozakiHiyamaKishi macrocyclization (95% yield) and an unexpected reagent-controlled reversible translactonization, which, being the first example within the cembranolide family, might have biogenetic implications and be of great importance to synthetic studies of the a-methylene-?-lactone-bearing cembranolides.

引用

页码：1966 / 1969

页数：4

共 50 条

[21] Total Synthesis and Structure Revision of Saniculamoid D [J].

Ota, Koichiro ;

Kamaike, Kazuo ;

Miyaoka, Hiroaki .

SYNLETT, 2023, 34 (19) :2304-2308

[22] Revision of the Structure and Total Synthesis of Topsentin C [J].

Golantsov, Nikita E. ;

Festa, Alexey A. ;

Varlamov, Alexey V. ;

Voskressensky, Leonid G. .

SYNTHESIS-STUTTGART, 2017, 49 (11) :2562-2574

[23] Catalytic Asymmetric Synthesis and Stereochemical Revision of (+)-Cryptoconcatone H [J].

-Felice, Franco Della ;

Sarotti, Ariel M. ;

Pilli, Ronaldo A. .

JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (17) :9191-9197

[24] Catalytic Asymmetric Crotylation of Aldehydes: Application in Total Synthesis of (-)-Elisabethadione [J].

O'Hora, Paul S. ;

Incerti-Pradillos, Celia A. ;

Kabeshov, Mikhail A. ;

Shipilovskikh, Sergei A. ;

Rubtsov, Aleksandr E. ;

Elsegood, Mark R. J. ;

Malkov, Andrei V. .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (12) :4551-4555

[25] Asymmetric Total Synthesis of (-)-Guignardones A and B [J].

Yan, Zhiming ;

Zhao, Chunbo ;

Gong, Jianxian ;

Yang, Zhen .

ORGANIC LETTERS, 2020, 22 (04) :1644-1647

[26] Asymmetric total synthesis of (+)-astellatol and (-)-astellatene [J].

Zhao, Nan ;

Xie, Shengling ;

Tian, Peilin ;

Tong, Rongbiao ;

Ning, Chengqing ;

Xu, Jing .

ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (12) :2014-2022

[27] Total Asymmetric Synthesis of Monosaccharides and Analogues [J].

Robina, Inmaculada ;

Carmona, Ana T. ;

Moreno-Vargas, Antonio J. ;

Moreno-Clavijo, Elena .

CHIMIA, 2011, 65 (1-2) :85-90

[28] Transannular reactions in asymmetric total synthesis [J].

Reyes, Efraim ;

Uria, Uxue ;

Carrillo, Luisa ;

Vicario, Jose L. .

TETRAHEDRON, 2014, 70 (50) :9461-9484

[29] A Concise Asymmetric Total Synthesis of (+)-Epilupinine [J].

Tsutsumi, Tomohiro ;

Karanjit, Sangita ;

Nakayama, Atsushi ;

Namba, Kosuke .

ORGANIC LETTERS, 2019, 21 (08) :2620-2624

[30] Asymmetric Total Synthesis of Antibiotic Elansolid A [J].

Wang, Liang-Liang ;

Yu, Qi ;

Zhang, Wenjing ;

Yang, Shuai ;

Peng, Lin ;

Zhang, Liang ;

Li, Xiao-Nian ;

Gagosz, Fabien ;

Kirschning, Andreas .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (15) :6871-6881

← 1 2 3 4 5 →