A rapid entry to C-prenylcarbazoles: total synthesis of clausamine C-D, clausevatine D and clausine F

被引：35

作者：

Jana, Amit Kumar ^{[1
]}

Mal, Dipakranjan ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kharagpur 721302, W Bengal, India

来源：

CHEMICAL COMMUNICATIONS | 2010年 / 46卷 / 24期

关键词：

TRANSITION-METAL-COMPLEXES; 1ST TOTAL-SYNTHESIS; ENANTIOSELECTIVE TOTAL-SYNTHESIS; CARBAZOLE ALKALOIDS; ORGANIC-SYNTHESIS; OXIDATIVE CYCLIZATION; ARYLATION; ROUTE; CARQUINOSTATIN; REARRANGEMENT;

D O I：

10.1039/c0cc00527d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The key prenylcarbazole precursor 33 was readily assembled from diester 30 by an ester-driven para-Claisen rearrangement followed by selective removal of the ester function. Unusual oxidative cyclization of 33 by m-CPBA resulted in the total synthesis of tetracyclic carbazole natural products 3 and 11.

引用

页码：4411 / 4413

页数：3

共 56 条

[1] Domino N-H/C-H bond activation: Palladium-catalyzed synthesis of annulated heterocycles using dichloro(hetero)arenes [J].

Ackermann, Lutz ;

Althammer, Andreas .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) :1627-1629

[2] Novel routes to pyrroles, indoles and carbazoles -: Applications in natural product synthesis [J].

Agarwal, S ;

Cämmerer, S ;

Filali, S ;

Fröhner, W ;

Knöll, J ;

Krahl, MP ;

Reddy, KR ;

Knölker, HJ .

CURRENT ORGANIC CHEMISTRY, 2005, 9 (15) :1601-1614

[3] CLAISEN REARRANGEMENT OF PRENYL ETHERS OF ISOMERIC ACETYLNAPHTHOLS AND BISPRENYL ETHERS OF 4,6-DIACETYLRESORCINOLS AND 2,4-DIACETYLRESORCINOLS [J].

ANJANEYULU, ASR ;

ISAA, BM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (09) :2089-2094

[4] GENERAL ROUTE TO SUBSTITUTED NAPHTHOLS [J].

BROOM, NJP ;

SAMMES, PG .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (04) :162-164

[5] Synthesis of Carbazoles by Intramolecular Arylation of Diarylamide Anions [J].

Buden, Maria E. ;

Vaillard, Victoria A. ;

Martin, Sandra E. ;

Rossi, Roberto A. .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (12) :4490-4498

[6] Claisen rearrangement over the past nine decades [J].

Castro, AMM .

CHEMICAL REVIEWS, 2004, 104 (06) :2939-3002

[7]

Chakraborty D.P., 1993, ALKALOIDS, V44, P257, DOI DOI 10.1016/S0099-9598(08)60146-7

[8] Carvedilol-liposome interaction: Evidence for strong association with the hydrophobic region of the lipid bilayers [J].

Cheng, HY ;

Randall, CS ;

Holl, WW ;

Constantinides, PP ;

Yue, TL ;

Feuerstein, GZ .

BIOCHIMICA ET BIOPHYSICA ACTA-BIOMEMBRANES, 1996, 1284 (01) :20-28

[9] Synthesis of carbazomycin B by radical arylation of benzene [J].

Crich, D ;

Rumthao, S .

TETRAHEDRON, 2004, 60 (07) :1513-1516

[10] Transition metal complexes inorganic synthesis, Part 77.: First enantioselective total synthesis of neocarazostatin B, determination of its absolute configuration and transformation into carquinostatin A [J].

Czerwonka, R ;

Reddy, KR ;

Baum, E ;

Knölker, HJ .

CHEMICAL COMMUNICATIONS, 2006, (07) :711-713

← 1 2 3 4 5 6 →