Synthesis of diversely functionalized indolizidinones and related bicyclic lactams using intramolecular Grubbs olefin metathesis and Dieckmann condensation

被引：56

作者：

Hanessian, S ^{[1
]}

Sailes, H ^{[1
]}

Munro, A ^{[1
]}

Therrien, E ^{[1
]}

机构：

[1] Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 19期

关键词：

D O I：

10.1021/jo030145z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bicyclic 1-aza-2-oxo ring systems with versatile functionality were synthesized from the Grubbs olefin metathesis of appropriate olefinic precursors, starting with L-pyroglutamic acid. The carbocyclization products were further functionalized utilizing the double bond or by enolate chemistry of the corresponding beta,gamma-unsaturated bicyclic lactam. In an alternative strategy, indolizidinones were synthesized by application of an intramolecular Dieckmann cyclization. A constrained peptidomimetic thrombin inhibitor was prepared from one of the bicyclic indolizidinones.

引用

页码：7219 / 7233

页数：15

共 74 条

[1] PYRROLIDINE BASED ANALOGS OF 3'-DEOXYTHYMIDINE [J].

ALTMANN, KH .

TETRAHEDRON LETTERS, 1993, 34 (48) :7721-7724

[2]

Armstrong SK, 1998, J CHEM SOC PERK T 1, P371

[3] A sequential electrochemical oxidation - Olefin metathesis strategy for the construction of bicyclic lactam based peptidomimetics [J].

Beal, LM ;

Moeller, KD .

TETRAHEDRON LETTERS, 1998, 39 (26) :4639-4642

[4] Anodic amide oxidation/olefin metathesis strategies: Developing a unified approach to the synthesis of bicyclic lactam peptidomimetics [J].

Beal, LM ;

Liu, B ;

Chu, WH ;

Moeller, KD .

TETRAHEDRON, 2000, 56 (52) :10113-10125

[5] Functionalised pyrrolidinones derived from (S)-pyroglutamic acid [J].

Beard, MJ ;

Bailey, JH ;

Cherry, DT ;

Moloney, MG ;

Shim, SB ;

Statham, KA ;

Bamford, MJ ;

Lamont, RB .

TETRAHEDRON, 1996, 52 (10) :3719-3740

[6] THE REFINED 1.9 A CRYSTAL-STRUCTURE OF HUMAN ALPHA-THROMBIN - INTERACTION WITH D-PHE-PRO-ARG CHLOROMETHYLKETONE AND SIGNIFICANCE OF THE TYR-PRO-PRO-TRP INSERTION SEGMENT [J].

BODE, W ;

MAYR, I ;

BAUMANN, U ;

HUBER, R ;

STONE, SR ;

HOFSTEENGE, J .

EMBO JOURNAL, 1989, 8 (11) :3467-3475

[7] A HIGHLY STEREOCONTROLLED, 4-STEP SYNTHESIS OF (+/-)-LASUBINE-II [J].

BROWN, JD ;

FOLEY, MA ;

COMINS, DL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (22) :7445-7447

[8] FLASH VACUUM THERMOLYSIS OF OXAZOLIDINES - A NEW WAY TO REACTIVE AZOMETHINE YLIDS - INTRAMOLECULAR CYCLOADDITION REACTIONS TOWARDS PYRROLIZIDINES SYNTHESIS [J].

BUREAU, R ;

MORTIER, J ;

JOUCLA, M .

TETRAHEDRON, 1992, 48 (41) :8947-8952

[9]

Chiesa MV, 1996, SYNLETT, P441

[10] The synthesis of bicyclic lactam based His-Pro building blocks: the effect of substituent polarity on an intramolecular bond migration [J].

Chu, WH ;

Moeller, KD .

TETRAHEDRON LETTERS, 1999, 40 (45) :7939-7943

← 1 2 3 4 5 6 7 8 →