Exploiting the reversibility of olefin metathesis.: Syntheses of macrocyclic trisubstituted alkenes and (R,R)-(-)-pyrenophorin

被引：123

作者：

Fürstner, A ^{[1
]}

Thiel, OR ^{[1
]}

Ackermann, L ^{[1
]}

机构：

[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 03期

关键词：

D O I：

10.1021/ol0069554

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The formation of the trisubstituted cycloalkene 7 by RCM of diene 5 proceeds via the acyclic dimer 6, thus demonstrating the ready reversibility of olefin metathesis if catalyzed by "second generation" ruthenium carbene complexes such as 2-4. When applied to acrylate 11, these catalysts trigger a cyclooligomerization process that evolves with time and serves as key step en route to the lactide antibiotic (-)-pyrenophorin 8.

引用

页码：449 / 451

页数：3

共 44 条

[1] Ruthenium carbene complexes with imidazol-2-ylidene ligands:: Syntheses of conduritol derivatives reveals superior RCM activity
Ackermann, L
El Tom, D
Fürstner, A
[J]. TETRAHEDRON, 2000, 56 (15) : 2195 - 2202
[2] Ruthenium carbene complexes with imidazolin-2-ylidene ligands allow the formation of tetrasubstituted cycloalkenes by RCM
Ackermann, L
Fürstner, A
Weskamp, T
Kohl, FJ
Herrmann, WA
[J]. TETRAHEDRON LETTERS, 1999, 40 (26) : 4787 - 4790
[3] [Anonymous], ANGEW CHEM
[4] BALDWIN JE, 1992, SYNLETT, P875
[5] Synthesis of functionalized olefins by cross and ring-closing metatheses
Chatterjee, AK
Morgan, JP
Scholl, M
Grubbs, RH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (15) : 3783 - 3784
[6] Synthesis of trisubstituted alkenes via olefin cross-metathesis
Chatterjee, AK
Grubbs, RH
[J]. ORGANIC LETTERS, 1999, 1 (11) : 1751 - 1753
[7] Total syntheses of (S)-(-)-zearalenone and lasiodiplodin reveal superior metathesis activity of ruthenium carbene complexes with imidazol-2-ylidene ligands
Fürstner, A
Thiel, OR
Kindler, N
Bartkowska, B
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (23) : 7990 - 7995
[8] Synthesis of 2-Hydroxy-6-{[(16R)-beta-D-mannopyranosyloxy]heptadecyl}benzoic acid, a fungal metabolite with GABA(A) ion channel receptor inhibiting properties
Furstner, A
Konetzki, I
[J]. TETRAHEDRON, 1996, 52 (48) : 15071 - 15078
[9] Asymmetric synthesis of the fully functional macrolide core of salicylihalamide:: Remote control of olefin geometry during RCM
Fürstner, A
Thiel, OR
Blanda, G
[J]. ORGANIC LETTERS, 2000, 2 (23) : 3731 - 3734
[10] Fürstner A, 2000, ANGEW CHEM INT EDIT, V39, P3012

← 1 2 3 4 5 →