Novel synthesis of bromoindolenine with spiro-β-lactam in chartelline

被引：31

作者：

Nishikawa, T ^{[1
]}

Kajii, S

Isobe, M

机构：

[1] Nagoya Univ, Grad Sch Bioagr Sci, Chikusa Ku, Nagoya, Aichi 4648601, Japan

[2] Japan Sci & Technol Agcy, JST, PRESTO, Kawaguchi 3320012, Japan

来源：

SYNLETT | 2004年 / 11期

关键词：

chartelline; indole; beta-lactam; cyclization; marine natural product;

D O I：

10.1055/s-2004-830885

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Model compounds containing an indolenine beta-lactam moiety in chartelline were synthesized by nucleophilic substitution at the nitrogen atom of O-sulfonylated hydroxamic acid prepared from 2-methylindole-3-acetic acid.

引用

页码：2025 / 2027

页数：3

共 15 条

[1] MARINE ALKALOIDS .12. CHARTELLINES, HALOGENATED BETA-LACTAM ALKALOIDS FROM THE MARINE BRYOZOAN CHARTELLA-PAPYRACEA [J].

ANTHONI, U ;

CHEVOLOT, L ;

LARSEN, C ;

NIELSEN, PH ;

CHRISTOPHERSEN, C .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (21) :4709-4712

[2] STEREOSPECIFIC CONVERSION OF PEPTIDES INTO BETA-LACTAMS [J].

BALDWIN, JE ;

AU, A ;

CHRISTIE, M ;

HABER, SB ;

HESSON, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (20) :5957-5958

[3]

BITTNER S, 1965, TETRAHEDRON LETT, V6, P95

[4] MARINE ALKALOIDS .10. CHARTELLINE-A - A PENTAHALOGENATED ALKALOID FROM THE MARINE BRYOZOAN CHARTELLA-PAPYRACEA [J].

CHEVOLOT, L ;

CHEVOLOT, AM ;

GAJHEDE, M ;

LARSEN, C ;

ANTHONI, U ;

CHRISTOPHERSEN, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (15) :4542-4543

[5] Solid-phase synthesis of Agel 416; a novel approach to modified polyamines [J].

Hone, ND ;

Payne, LJ .

TETRAHEDRON LETTERS, 2000, 41 (32) :6149-6152

[6] Model studies on total synthesis of the chartellines, spirocyclic β-lactam alkaloids from a marine bryozoan [J].

Lin, XC ;

Weinreb, SM .

TETRAHEDRON LETTERS, 2001, 42 (14) :2631-2633

[7] BIOGENETIC-TYPE SYNTHESIS OF PENICILLIN-CEPHALOSPORIN ANTIBIOTICS .1. STEREOCONTROLLED SYNTHESIS OF PENAM-RING AND CEPHEM-RING SYSTEMS FROM AN ACYCLIC TRIPEPTIDE EQUIVALENT [J].

NAKATSUKA, S ;

TANINO, H ;

KISHI, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (17) :5008-5010

[8] BIOGENETIC-TYPE SYNTHESIS OF PENICILLIN-CEPHALOSPORIN ANTIBIOTICS .2. OXIDATIVE CYCLIZATION ROUTE TO BETA-LACTAM THIAZOLINE DERIVATIVES [J].

NAKATSUKA, S ;

TANINO, H ;

KISHI, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (17) :5010-5012

[9] Synthesis of model compound containing an indole spiro-β-lactam moiety with vinylchloride in chartellines [J].

Nishikawa, T ;

Kajii, S ;

Isobe, M .

CHEMISTRY LETTERS, 2004, 33 (04) :440-441

[10]

PIPER JR, 1966, J HETEROCYCLIC CHEM, P95

← 1 2 →