Total Synthesis of (-)-Crinipellin A

被引：63

作者：

Kang, Taek ^{[1
]}

Song, Seog Boem ^{[1
]}

Kim, Won-Yeob ^{[1
]}

Kim, Byung Gyu ^{[1
]}

Lee, Hee-Yoon ^{[1
]}

机构：

[1] Korea Adv Inst Sci & Technol, Dept Chem, Taejon 305701, South Korea

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2014年 / 136卷 / 29期

基金：

新加坡国家研究基金会;

关键词：

1,3-DIYL TRAPPING REACTION; TRIMETHYLENEMETHANE DIYLS; CYCLOADDITION REACTIONS; ASYMMETRIC INDUCTION; CARBONYL-COMPOUNDS; DIAZO-COMPOUNDS; IDEAL SYNTHESIS; CRINIPELLIN B; TRIQUINANES; OXIDATION;

D O I：

10.1021/ja5054412

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first total synthesis of (-)-crinipellin A is described. The tetraquinane core skeleton of crinipellin A was assembled through the tandem [2 + 3] cycloaddition reaction of an allenyl diazo substrate containing a cyclopentane ring in a single operation. The absolute stereochemistry was confirmed through the total synthesis.

引用

页码：10274 / 10276

页数：3

共 38 条

[11] Cycloaddition reactions of trimethylenemethane diyls generated from alkynyl iodonium salts [J].

Lee, Hee-Yoon ;

Yoon, Yeokwon ;

Lim, Yeon-Hee ;

Lee, Yonghan .

TETRAHEDRON LETTERS, 2008, 49 (39) :5693-5696

[12] Triquinanes from linear ketones via trimethylenemethane diyls [J].

Lee, Hee-Yoon ;

Kim, Won-Yeob ;

Lee, Sejin .

TETRAHEDRON LETTERS, 2007, 48 (08) :1407-1410

[13] Angularly Fused Triquinanes from Linear Substrates through Trimethylenemethane Diyl [2+3] Cycloaddition Reaction [J].

Lee, Hee-Yoon ;

Jung, Yongsik ;

Yoon, Yeokwon ;

Kim, Byung Gyu ;

Kim, Yeonjoon .

ORGANIC LETTERS, 2010, 12 (11) :2672-2674

[14] Triquinanes from linear alkylidene carbenes via trimethylenemethane diyls [J].

Lee, HY ;

Kim, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (34) :10156-10157

[15] Four Novel Diterpenoids from Crinipellis sp. 113 [J].

Li, Yao-Yao ;

Shen, Yue-Mao .

HELVETICA CHIMICA ACTA, 2010, 93 (11) :2151-2157

[16]

LITTLE RD, 1992, SYNLETT, P107

[17]

LITTLE RD, 1983, J AM CHEM SOC, V105, P6976, DOI 10.1021/ja00361a047

[18]

MANCUSO AJ, 1981, SYNTHESIS-STUTTGART, P165

[19] LINEARLY FUSED VS BRIDGED REGIOSELECTION IN THE INTRAMOLECULAR 1,3-DIYL TRAPPING REACTION [J].

MASJEDIZADEH, MR ;

DANNECKERDOERIG, I ;

LITTLE, RD .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (09) :2742-2752

[20] SYNTHETIC APPROACH TO NOVEL CRINIPELLIN DITERPENES - CONSTRUCTION OF THE FUNCTIONALIZED C20-TETRAQUINANE FRAMEWORK [J].

MEHTA, G ;

RAO, KS ;

REDDY, MS .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (04) :693-700

← 1 2 3 4 →