Transannular rearrangement of activated 2,5-diketopiperazines: a key route to original scaffolds

被引：29

作者：

Farran, Daniel ^{[1
]}

Parrot, Isabelle ^{[1
]}

Toupet, Loic ^{[2
]}

Martinez, Jean ^{[1
]}

Dewynter, Georges ^{[1
]}

机构：

[1] Univ Montpellier 2, Univ Montpellier 1, Inst Biomol Max Mousseron, UMR CNRS 5247, F-34095 Montpellier 5, France

[2] Univ Rennes 1, Grp Mat Condensee & Mat, UMR6626, F-35042 Rennes, France

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2008年 / 6卷 / 21期

关键词：

D O I：

10.1039/b810352f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and original stereocontrolled transannular rearrangement starting from activated 2,5-diketopiperazines has been developed, an opportunity for the medicinal chemistry field, which requests access to novel biological scaffolds. This powerful ring contraction, which can be related to a stereoselective aza-version of the Chan rearrangement, allows for example the one-step synthesis of various tetramic acids, access to 2-disubstituted statins, or the synthesis of relevant lactam-constrained dipeptide mimetics using a TRAL-RCM sequence.

引用

页码：3989 / 3996

页数：8

共 45 条

[31] Stereo-divergent synthesis of L-threo- and L-erythro-[2,3-2H2]amino acids using optically active dioxopiperazine as a chiral template
Oba, M
Terauchi, T
Owari, Y
Imai, Y
Motoyama, I
Nishiyama, K
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (07): : 1275 - 1281
[32] Asymmetric synthesis of functionalized aza-cyclic amino acids with quaternary stereocenters by a phase-transfer-catalyzed alkylation strategy
Ooi, T
Miki, T
Maruoka, K
[J]. ORGANIC LETTERS, 2005, 7 (02) : 191 - 193
[33] Cyclic amino acid derivatives
Park, KH
Kurth, MJ
[J]. TETRAHEDRON, 2002, 58 (43) : 8629 - 8659
[34] Phillips AJ, 1999, ALDRICHIM ACTA, V32, P75
[35] Peptidomimetic design
Ripka, AS
Rich, DH
[J]. CURRENT OPINION IN CHEMICAL BIOLOGY, 1998, 2 (04) : 441 - 452
[36] NATURALLY-OCCURRING TETRAMIC ACIDS - STRUCTURE, ISOLATION, AND SYNTHESIS
ROYLES, BJL
[J]. CHEMICAL REVIEWS, 1995, 95 (06) : 1981 - 2001
[37] Ruthenium-catalyzed ring closing olefin metathesis of non-natural alpha-amino acids
Rutjes, FPJT
Schoemaker, HE
[J]. TETRAHEDRON LETTERS, 1997, 38 (04) : 677 - 680
[38] SAWYER TK, 1997, STRUCTURE BASED DRUG, V1, P559
[39] Synthesis and reactivity of C-heteroatom-substituted aziridines
Singh, Girija S.
D'hooghe, Matthias
De Kimpe, Norbert
[J]. CHEMICAL REVIEWS, 2007, 107 (05) : 2080 - 2135
[40] Pyrrolidines bearing a quaternary α-stereogenic center.: Part 2.: Access to proline chimeras, stereoselective approach and mechanistic aspects
Trancard, D
Tout, JB
Giard, T
Chichaoui, I
Cahard, D
Plaquevent, JC
[J]. TETRAHEDRON LETTERS, 2000, 41 (20) : 3843 - 3847

← 1 2 3 4 5 →