A concise and straightforward approach to total synthesis of (+)-Strictifolione and formal synthesis of Cryptofolione via a unified strategy

被引：6

作者：

Li, Xiaotong ^{[1
]}

Wang, Gaopeng ^{[1
]}

Zhang, Zhibin ^{[1
]}

Wu, Na ^{[3
]}

Yang, Qianqian ^{[2
]}

Huang, Shuangping ^{[1
]}

Wang, Xiaoji ^{[2
]}

机构：

[1] Jiangxi Sci & Technol Normal Univ, Sch Pharm, Nanchang, Jiangxi, Peoples R China

[2] Jiangxi Sci & Technol Normal Univ, Sch Life Sci, Nanchang, Jiangxi, Peoples R China

[3] Guangxi Normal Univ, Sch Chem & Pharmaceut Sci, Key Lab Chem & Mol Engn Med Resources, Guilin, Peoples R China

来源：

SYNTHETIC COMMUNICATIONS | 2019年 / 49卷 / 08期

基金：

美国国家科学基金会;

关键词：

Strictifolione; Cryptofolione; total synthesis; Barbier reaction; olefin cross-metathesis; STEREOSELECTIVE TOTAL-SYNTHESIS; ASYMMETRIC-SYNTHESIS; (+)-CRYPTOFOLIONE; EFFICIENT;

D O I：

10.1080/00397911.2019.1580373

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe a concise and straightforward approach to the total syntheses of (+)-Strictifolione and Cryptofolione in the longest linear sequences of four steps and six steps from 3-phenyl propanal and trans-cinnamaldehyde, respectively. The route utilized a titanium tetraisopropoxide/(R)-[1,1'-binaphthalene]-2,2'-diol catalyzed Mukaiyama aldol reaction, indium(0)-promoted Barbier reaction, and olefin cross-metathesis as the key reactions. [GRAPHICS] .

引用

页码：1031 / 1039

页数：9

共 33 条

[1] Efficient Stereoselective Total Synthesis of (+)-Cryptofolione and the First Synthesis of (-)-Cryptocaryalactone [J].

Balasubramanyam, P. ;

Reddy, Gandolla Chinna ;

Salvanna, Nayaki ;

Das, Biswanath .

SYNTHESIS-STUTTGART, 2011, (22) :3706-3710

[2] NATURALLY OCCURRING TERPENE DERIVATIVES .189. NEW BISABOLENE DERIVATIVE AND NEW DIHYDROCAFFEIC ACID-DERIVATIVE FROM TARCHONANTHUSTRILOBUS [J].

BOHLMANN, F ;

SUWITA, A .

PHYTOCHEMISTRY, 1979, 18 (04) :677-678

[3] Total synthesis of (+)-strictifolione [J].

BouzBouz, S ;

Cossy, J .

ORGANIC LETTERS, 2003, 5 (11) :1995-1997

[4] Stereoselective total synthesis of (+)-cryptofolione and (+)-goniothalamin [J].

Das, Biswanath ;

Nagendra, Siddavatam ;

Reddy, Cheruku Ravindra .

TETRAHEDRON-ASYMMETRY, 2011, 22 (11) :1249-1254

[5] Stereoselective total synthesis of (+)-strictifolione and (6R)-6[(E,4R,6R)-4,6-dihydro-10-phenyl-1-decenyl)-5,6-dihydro-2H-2-pyrone [J].

Das, Biswanath ;

Veeranjaneyulu, Boyapati ;

Balasubramanyam, Penagaluri ;

Srilatha, Malampati .

TETRAHEDRON-ASYMMETRY, 2010, 21 (23) :2762-2767

[6] Passifloricins, polyketides α-pyrones from Passiflora foetida resin [J].

Echeverri, F ;

Arango, V ;

Quiñones, W ;

Torres, F ;

Escobar, G ;

Rosero, Y ;

Archbold, R .

PHYTOCHEMISTRY, 2001, 56 (08) :881-885

[7] Efficient asymmetric syntheses of (+)-strictifolione [J].

Enders, D ;

Lenzen, A ;

Müller, M .

SYNTHESIS-STUTTGART, 2004, (09) :1486-1496

[8]

FU X, 1993, PHYTOCHEMISTRY, V33, P1272, DOI 10.1016/0031-9422(93)85065-Y

[9] A chemoenzymatic asymmetric synthesis of (+)-strictifolione [J].

Ghadigaonkar, Sneha ;

Koli, Mrunesh R. ;

Gamre, Sunita S. ;

Choudhary, Manoj K. ;

Chattopadhyay, Subrata ;

Sharma, Anubha .

TETRAHEDRON-ASYMMETRY, 2012, 23 (14) :1093-1099

[10] A Concise and Versatile Total Synthesis of All Stereoisomers of Tarchonanthuslactone [J].

Huang, Shuangping ;

Liu, Dongwang ;

Tang, Linjun ;

Huang, Feifei ;

Yang, Wei ;

Wang, Xiaoji .

SYNLETT, 2015, 26 (14) :2019-2023

← 1 2 3 4 →