Synthetic applications of 3,4-dihalo-2(5H)-furanones:: A formal total synthesis of nostoclides I and II

被引：24

作者：

Bellina, F ^{[1
]}

Rossi, R ^{[1
]}

机构：

[1] Univ Pisa, Dipartimento Chim & Chim Ind, I-56126 Pisa, Italy

来源：

SYNTHESIS-STUTTGART | 2002年 / 18期

关键词：

2(5H)-furanones; cross-coupling; regioselectivity; Stille reaction; benzylation;

D O I：

10.1055/s-2002-35994

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-Benzyl-4-isopropyl-2(5H)-furanone, which is a precursor to two naturally-occurring cytotoxic (Z)-5-ylidene-2(5H)furanone derivatives, has been conveniently prepared from 3,4-dibromo-2(5H)-furanone by a three-step procedure involving two Pd-catalyzed cross-coupling reactions and a Rh(I)-catalyzed hydrogenation.

引用

页码：2729 / 2732

页数：4

共 23 条

[1] Total synthesis of rubrolide M and some of its unnatural congeners
Bellina, F
Anselmi, C
Rossi, R
[J]. TETRAHEDRON LETTERS, 2002, 43 (11) : 2023 - 2027
[2] Selective synthesis of (Z)-4-aryl-5-[1-(aryl)methylidene]-3-bromo-2(5H)-furanones
Bellina, F
Anselmi, C
Viel, S
Mannina, L
Rossi, R
[J]. TETRAHEDRON, 2001, 57 (50) : 9997 - 10007
[3] Synthesis of 4-alkyl-3-bromo-2(5H)-furanones and unsymmetrically disubstituted 3,4-dialkyl-2(5H)-furanones by palladium-catalyzed cross-coupling reactions
Bellina, F
Anselmi, C
Rossi, R
[J]. TETRAHEDRON LETTERS, 2001, 42 (23) : 3851 - 3854
[4] BELLINA F, 2002, TRANSM C HET CHEM BA
[5] FURANOLATE-BASED STRATEGY FOR SEQUENTIAL 2,3,4-TRISUBSTITUTION OF BUTENOLIDE - TOTAL SYNTHESIS OF NOSTOCLIDE-I AND NOSTOCLIDE-II
BOUKOUVALAS, J
MALTAIS, F
LACHANCE, N
[J]. TETRAHEDRON LETTERS, 1994, 35 (43) : 7897 - 7900
[6] The synthesis of γ-alkylidenebutenolides
Brückner, R
[J]. CURRENT ORGANIC CHEMISTRY, 2001, 5 (06) : 679 - 718
[7] Dynamical explanation and mental representations
Chemero, A
[J]. TRENDS IN COGNITIVE SCIENCES, 2001, 5 (04) : 141 - 142
[8] OBSERVATIONS REGARDING THE REGIOCHEMICAL AND STEREOCHEMICAL COURSE OF THE CYCLIZATION OF COMPLEX 5-HEXENYL RADICALS - AN APPROACH TO PERHYDRONAPHTHALENES
CHUANG, CP
GALLUCCI, JC
HART, DJ
HOFFMAN, C
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (14) : 3218 - 3226
[9] THE PREPARATION OF PURE ALLYL-TYPE AND BENZYL-TYPE ORGANOALKALI INTERMEDIATES VIA ORGANOTIN COMPOUNDS
DESPONDS, O
SCHLOSSER, M
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1991, 409 (1-2) : 93 - 101
[10] STRUCTURE DETERMINATION OF SEIRIDIN AND ISOSEIRIDIN, PHYTOTOXIC BUTENOLIDES FROM CULTURE FILTRATE OF SEIRIDIUM-CARDINALE
EVIDENTE, A
RANDAZZO, G
BALLIO, A
[J]. JOURNAL OF NATURAL PRODUCTS, 1986, 49 (04): : 593 - 601

← 1 2 3 →