Biomimetic tandem cyclization catalyzed by Hg(OTf)2 affording polycarbocycles

被引：31

作者：

Imagawa, H ^{[1
]}

Iyenaga, T ^{[1
]}

Nishizawa, M ^{[1
]}

机构：

[1] Tokushima Bunri Univ, Fac Pharmaceut Sci, Tokushima 7708514, Japan

来源：

SYNLETT | 2005年 / 04期

关键词：

biomimetic; cyclization; alkyne; mercuric triflate; catalysis;

D O I：

10.1055/s-2005-863703

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Efficient biomimetic tandem cyclization catalyzed by Hg(OTf)(2) was achieved to give tricyclic 4 and tetractyclic 6 in high catalytic turnover. Structures of cyclization products were confirmed by X-ray diffraction study.

引用

页码：703 / 705

页数：3

共 36 条

[1] ETHYLIDYNE ALKYNES FROM ISOPROPYLIDENE OLEFINS [J].

ABIDI, SL .

TETRAHEDRON LETTERS, 1986, 27 (03) :267-270

[2] NITROSATIVE ELIMINATION OF TERPENYL ALKANOLAMINES LEADING TO ALKYNYL N-NITROSO-ANALOGS [J].

ABIDI, SL .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (18) :1222-1223

[3] DIRECT CONVERSION OF TERPENYLALKANOLAMINES TO ETHYLIDYNE N-NITROSO COMPOUNDS [J].

ABIDI, SL .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (14) :2687-2694

[4] A TOTAL SYNTHESIS OF THE SESQUITERPENE QUINONE METACHROMIN-A [J].

ALMEIDA, WP ;

CORREIA, CRD .

TETRAHEDRON LETTERS, 1994, 35 (09) :1367-1370

[5]

BARTLETT PA, 1984, ASYMMETRIC SYNTHESIS, V3, P341

[6] 2,3-OXIDOSQUALENE AN INTERMEDIATE IN BIOLOGICAL SYNTHESIS OF STEROLS FROM SQUALENE [J].

COREY, EJ ;

RUSSEY, WE ;

DEMONTEL.PR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (20) :4750-&

[7] MECHANISM OF THE NITROUS ACID-INDUCED DEALKYLATION OF TRISUBSTITUTED (TERMINAL ISOPROPYLIDENE) OLEFINS TO FORM ACETYLENES [J].

COREY, EJ ;

SEIBEL, WL ;

KAPPOS, JC .

TETRAHEDRON LETTERS, 1987, 28 (42) :4921-4924

[8] MIGRATION AND ELIMINATION OF HYDROGEN DURING BIOSYNTHESIS OF CHOLESTEROL FROM SQUALENE [J].

CORNFORT.JW ;

CORNFORT.RH ;

DONNINGE.C ;

POPJAK, G ;

SHIMIZU, Y ;

ICHII, S ;

FORCHIEL.E ;

CASPI, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (14) :3224-+

[9] ZUR KENNTNIS DER TRITERPENE .190. EINE STEREOCHEMISCHE INTERPRETATION DER BIOGENETISCHEN ISOPRENREGEL BEI DEN TRITERPENEN [J].

ESCHENMOSER, A ;

RUZICKA, L ;

JEGER, O ;

ARIGONI, D .

HELVETICA CHIMICA ACTA, 1955, 38 (07) :1890-1904

[10] An exceptionally short and simple enantioselective total synthesis of pentacyclic triterpenes of the β-amyrin family [J].

Huang, AX ;

Xiong, ZM ;

Corey, EJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (43) :9999-10003

← 1 2 3 4 →