Synthesis of leprapinic acid, calycine and analogues by sequential [3+2]cyclization/suzuki/lactonization" reactions

被引：14
作者：
Ahmed, Z
Albrecht, U
Langer, P
机构：
[1] Univ Rostock, Inst Chem, D-18059 Rostock, Germany
[2] Ernst Moritz Arndt Univ Greifswald, Inst Chem & Biochem, D-17489 Greifswald, Germany
[3] Univ Rostock, Leibniz Inst Organ Katalyse, D-18059 Rostock, Germany
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 2005卷 / 16期
关键词：
butenolides; cyclizations; heterocycles; lactones; natural products; leprapinic acid;
D O I：
10.1002/ejoc.200500142
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Calycine and analogues were prepared on the basis of Suzuki cross-coupling reactions of gamma-alkylidene-alpha-hydroxybutenolides - readily available by cyclization of 1,3-dicarbonyl dianions or 1,3-bis(silyl enol ether)s with oxalyl derivatives and subsequent boron tribromide-mediated lactonization.
引用
收藏
页码：3469 / 3474
页数：6
相关论文
共 36 条
[1]   CONSTITUTION OF LEPRAPINIC ACID [J].
AGARWAL, SC ;
SESHADRI, TR .
TETRAHEDRON, 1965, 21 (11) :3205-&
[2]   Synthesis of natural pulvinic acids based on a '[3+2] cyclization-Suzuki cross-coupling' strategy [J].
Ahmed, Z ;
Langer, P .
TETRAHEDRON, 2005, 61 (08) :2055-2063
[3]   Suzuki cross-coupling reactions of γ-alkylidenebutenolides:: Application to the synthesis of vulpinic acid [J].
Ahmed, Z ;
Langer, P .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (11) :3753-3757
[4]   STUDIES ON CHEMISTRY OF LICHENS .14. STRUCTURE OF CALYCIN [J].
AKERMARK, B .
ACTA CHEMICA SCANDINAVICA, 1961, 15 (08) :1695-&
[5]  
[Anonymous], 1987, PROG CHEM ORG NAT PR
[6]   CONSTITUENTS OF HIGHER FUNGI .9. BOVINONE, 2,5-DIHYDROXY-3-GERANYLGERANYL-1,4-BENZOQUINONE FROM BOLETUS (SUILLUS) BOVINUS (LINN EX FR) KUNTZE [J].
BEAUMONT, PC ;
EDWARDS, RL .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (18) :2398-&
[7]   CONSTITUENTS OF HIGHER FUNGI .8. BLUEING OF BOLETUS SPECIES . VARIEGATIC ACID A HYDROXYTETRONIC ACID FROM BOLETUS SPECIES AND A REASSESSMENT OF STRUCTURE OF BOLETOL [J].
BEAUMONT, PC ;
EDWARDS, RL ;
ELSWORTHY, GC .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (24) :2968-+
[8]   The β-elimination route to stereodefined γ-alkylidenebutenolides [J].
Brückner, R .
CHEMICAL COMMUNICATIONS, 2001, (02) :141-152
[9]   The synthesis of γ-alkylidenebutenolides [J].
Brückner, R .
CURRENT ORGANIC CHEMISTRY, 2001, 5 (06) :679-718
[10]   CHEMISTRY OF ENOL SILYL ETHERS .5. A NOVEL CYCLOAROMATIZATION REACTION - REGIOCONTROLLED SYNTHESIS OF SUBSTITUTED METHYL SALICYLATES [J].
CHAN, TH ;
BROWNBRIDGE, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (10) :3534-3538
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