Synthesis of (+/-)-coerulescine and a formal synthesis of (+/-)-horsfiline

被引：69

作者：

Chang, MY ^{[1
]}

Pai, CL

Kung, YH

机构：

[1] Natl Univ Kaohsiung, Dept Appl Chem, Kaohsiung 811, Taiwan

[2] Natl Sun Yat Sen Univ, Dept Chem, Kaohsiung 804, Taiwan

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 49期

关键词：

coerulescine; horsfiline; 4-hydroxypiperidine; Lewis acid catalyzed rearrangement; 3-formyl-3-phenylpyrrolidine; 3,4-dihydroxy-4-phenylpiperidine;

D O I：

10.1016/j.tetlet.2005.10.015

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A straightforward synthesis of (+/-)-coerulescine and (+/-)-horsfiline has been established from 3-formyl-3-phenylpyrridine employing 4-hydroxypiperidine as the starting material. There are two remarkable steps for the synthesis of (+/-)-coerulescine and ()-horsfiline. One is the rapid access to produce 3-formyl-3-phenylpyrrolidine by Lewis acid-catalyzed rearrangement of 3,4-dihydroxy-4-phenylpiperidine. The other key step is an intramolecular electrophilic cyclization from 3-benzylcarbamoyl-3-plienylpyrrolidine to the 3,3-spirocyclic 2-oxindole ring skeleton. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：8463 / 8465

页数：3

共 45 条

[1] Oxindoles from Phalaris coerulescens [J].

Anderton, N ;

Cockrum, PA ;

Colegate, SM ;

Edgar, JA ;

Flower, K ;

Vit, I ;

Willing, RI .

PHYTOCHEMISTRY, 1998, 48 (03) :437-439

[2]

BASCOP SI, 1994, HETEROCYCLES, V38, P725

[3] An approach to some spiro oxindole alkaloids through cycloaddition reactions of 3-methylideneindolin-2-one [J].

Bell, SEV ;

Brown, RFC ;

Eastwood, FW ;

Horvath, JM .

AUSTRALIAN JOURNAL OF CHEMISTRY, 2000, 53 (03) :183-190

[4] From peptides to non-peptide peptidomimetics: Design and synthesis of new piperidine inhibitors of aspartic peptidases [J].

Bursavich, MG ;

West, CW ;

Rich, DH .

ORGANIC LETTERS, 2001, 3 (15) :2317-2320

[5]

Colegate SM, 1999, AUST VET J, V77, P537

[6] A convenient route to spiropyrrolidinyl-oxindole alkaloids via C-3 substituted ene-pyrrolidine carbamate radical cyclization [J].

Cossy, J ;

Cases, M ;

Pardo, DG .

TETRAHEDRON LETTERS, 1998, 39 (16) :2331-2332

[7] Azomethine ylide cycloaddition/reductive heterocyclization approach to oxindole alkaloids: Asymmetric synthesis of (-)-horsfiline [J].

Cravotto, G ;

Giovenzana, GB ;

Pilati, T ;

Sisti, M ;

Palmisano, G .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (25) :8447-8453

[8] 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

[9] 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

[10]

DUPONT PL, 1977, ACTA CRYSTALLOGR B, V33, P1801

← 1 2 3 4 5 →