Stereoselective Synthesis of the Benzodihydropentalene Core of the Fijiolides

被引：16

作者：

Kurzawa, Timon ^{[1
]}

Harms, Klaus ^{[1
]}

Koert, Ulrich ^{[1
]}

机构：

[1] Philipps Univ Marburg, Fachbereich Chem, Hans Meerwein Str 4, D-35043 Marburg, Germany

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 05期

关键词：

C-1027; CHROMOPHORE; HYDROXY KETONES; ISOMERIZATION; REDUCTION; LIGANDS;

D O I：

10.1021/acs.orglett.8b00163

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient stereoselective synthesis of the enantiomer of the benzodihydropentalene core of fijiolides A and B has been achieved. The asymmetric conjugate addition of styrylboronic acid to an indenone produced the first stereocenter. Ring C was installed by ring-closing metathesis of a cis disubstituted indanone. Regioselective epoxide opening by NaSePh and subsequent oxidative elimination produced an allylic alcohol. The final introduction of the cyclopentadiene was possible by elimination of an in situ formed triflate.

引用

页码：1388 / 1391

页数：4

共 24 条

[1] DIMETHYLDIOXIRANE OXIDATION OF TITANIUM ENOLATES - DIASTEREOSELECTIVE ALPHA-HYDROXYLATIONS [J].

ADAM, W ;

MULLER, M ;

PRECHTL, F .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (09) :2358-2364

[2] An efficient 1,2-chelation-controlled reduction of protected hydroxy ketones via Red-Al [J].

Bajwa, Naval ;

Jennings, Michael P. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (09) :3638-3641

[3] CONCERNING 1,5-DIDEHYDRO[10]ANNULENE SYSTEM [J].

DARBY, N ;

KIM, CU ;

SALAUN, JA ;

SHELTON, KW ;

TAKADA, S ;

MASAMUNE, S .

JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (23) :1516-&

[4] PREPARATION OF CONJUGATED DIENES FROM TOSYLHYDRAZONES OF ALPHA BETA-UNSATURATED KETONES AND ALKYLLITHIUM REAGENTS [J].

DAUBEN, WG ;

LORBER, ME ;

VIETMEYE.ND ;

SHAPIRO, RH ;

DUNCAN, JH ;

TOMER, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (17) :4762-&

[5] Chiral [2.2.2] dienes as ligands for Rh(I) in conjugate additions of boronic acids to a wide range of acceptors [J].

Defieber, C ;

Paquin, JF ;

Serna, S ;

Carreira, EM .

ORGANIC LETTERS, 2004, 6 (21) :3873-3876

[6] DIRECTED REDUCTION OF BETA-HYDROXY KETONES EMPLOYING TETRAMETHYLAMMONIUM TRIACETOXYBOROHYDRIDE [J].

EVANS, DA ;

CHAPMAN, KT ;

CARREIRA, EM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) :3560-3578

[7] Stereoselective isomerizations of 4-(2′-chloro-3′-methoxyphenyl)-2,5-dimethyl-1,3-dioxolanes:: Stereochemistry and conformation of the product 2-benzopyrans [J].

Giles, RGF ;

Green, IR ;

Li, SH .

AUSTRALIAN JOURNAL OF CHEMISTRY, 2005, 58 (08) :565-571

[8] Rhodium-catalyzed asymmetric 1,4-addition and its related asymmetric reactions [J].

Hayashi, T ;

Yamasaki, K .

CHEMICAL REVIEWS, 2003, 103 (08) :2829-2844

[9] Synthesis of Fijiolide A via an Atropselective Paracyclophane Formation [J].

Heinz, Christoph ;

Cramer, Nicolai .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (35) :11278-11281

[10] Protecting-Group-Free and Catalysis-Based Total Synthesis of the Ecklonialactones [J].

Hickmann, Volker ;

Alcarazo, Manuel ;

Fuerster, Alois .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (32) :11042-11044

← 1 2 3 →