The N-acyliminium Pictet-Spengler condensation as a multicomponent combinatorial reaction on solid phase and its application to the synthesis of demethoxyfumitremorgin C analogues

被引：133

作者：

Wang, HS ^{[1
]}

Ganesan, A ^{[1
]}

机构：

[1] Natl Univ Singapore, Inst Mol & Cell Biol, Singapore 117609, Singapore

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 10期

关键词：

D O I：

10.1021/ol991030d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] L-Tryptophan immobilized on polystyrene-Wang resin was sequentially reacted with an aldehyde and Fmoc-amino acid chloride, This generates a transient N-acyliminium species which undergoes Pictet-Spengler condensation to give a mixture of cis and trans tetrahydro-beta-carbolines. Removal of the Fmoc protecting group, with concomitant diketopiperazine formation, results in cyclative cleavage of the desired products from the resin.

引用

页码：1647 / 1649

页数：3

共 28 条

[1] Solid-phase organic reactions III: A review of the literature Nov 96 Dec 97 [J].

Booth, S ;

Hermkens, PHH ;

Ottenheijm, HCJ ;

Rees, DC .

TETRAHEDRON, 1998, 54 (51) :15385-15443

[2]

Brown RCD, 1998, J CHEM SOC PERK T 1, P3293

[3] ((9-FLUORENYLMETHYL)OXY)CARBONYL (FMOC) AMINO-ACID CHLORIDES - SYNTHESIS, CHARACTERIZATION, AND APPLICATION TO THE RAPID SYNTHESIS OF SHORT PEPTIDE SEGMENTS [J].

CARPINO, LA ;

COHEN, BJ ;

STEPHENS, KE ;

SADATAALAEE, SY ;

TIEN, JH ;

LANGRIDGE, DC .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (19) :3732-3734

[4] THE PICTET-SPENGLER CONDENSATION - A NEW DIRECTION FOR AN OLD REACTION [J].

COX, ED ;

COOK, JM .

CHEMICAL REVIEWS, 1995, 95 (06) :1797-1842

[5] Spirotryprostatin B, a novel mammalian cell cycle inhibitor produced by Aspergillus fumigatus [J].

Cui, CB ;

Kakeya, H ;

Osada, H .

JOURNAL OF ANTIBIOTICS, 1996, 49 (08) :832-835

[6] Novel mammalian cell cycle inhibitors, cyclotryprostatins A-D, produced by Aspergillus fumigatus, which inhibit mammalian cell cycle at G2/M phase [J].

Cui, CB ;

Kakeya, H ;

Osada, H .

TETRAHEDRON, 1997, 53 (01) :59-72

[7] Novel mammalian cell cycle inhibitors, spirotryprostatins A and B, produced by Aspergillus fumigatus, which inhibit mammalian cell cycle at G2/M phase [J].

Cui, CB ;

Kakeya, H ;

Osada, H .

TETRAHEDRON, 1996, 52 (39) :12651-12666

[8] Novel mammalian cell cycle inhibitors, tryprostatins A, B and other diketopiperazines produced by Aspergillus fumigatus .1. Taxonomy, fermentation, isolation and biological properties [J].

Cui, CB ;

Kakeya, H ;

Okada, G ;

Onose, R ;

Osada, H .

JOURNAL OF ANTIBIOTICS, 1996, 49 (06) :527-533

[9] TRYPROSTATIN-A AND TRYPROSTATIN-B, NOVEL MAMMALIAN-CELL CYCLE INHIBITORS PRODUCED BY ASPERGILLUS-FUMIGATUS [J].

CUI, CB ;

KAKEYA, H ;

OKADA, G ;

ONOSE, R ;

UBUKATA, M ;

TAKAHASHI, I ;

ISONO, K ;

OSADA, H .

JOURNAL OF ANTIBIOTICS, 1995, 48 (11) :1382-1384

[10]

Dax SL, 1999, CURR MED CHEM, V6, P255

← 1 2 3 →