A synthetic strategy using Witkop's pyrroloindole for (-)-debromoflustramine B, (+)-ent-debromoflustramine B and (+)-ent-debromoflustramide B

被引：22

作者：

Cardoso, A. Sofia P. ^{[1
,2
]}

Marques, M. Manuel B. ^{[1
,3
]}

Srinivasan, Natarajan ^{[1
]}

Prabhakar, Sundaresan ^{[1
,3
]}

Lobo, Ana M. ^{[1
,3
]}

机构：

[1] Univ Nova Lisboa, Fac Sci & Technol, REQUIMTE CQFB, Dept Chem, P-2829516 Monte De Caparica, Portugal

[2] Inst Nacl Saude Dr Ricardo Jorge, Ctr Qualadade Hidrica, Lab Quim & Toxicol, P-1649016 Lisbon, Portugal

[3] Univ Nova Lisboa, SINTOR, P-2829516 Monte De Caparica, Portugal

来源：

TETRAHEDRON | 2007年 / 63卷 / 41期

关键词：

D O I：

10.1016/j.tet.2007.07.091

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

While prenylation of (-)-Witkop's pyrroloindole (2), secured from L-tryptophan under standard N-alkylation conditions, led to a ca. 1: 1 diastereoisomeric mixture of two C-3a-alkylated indolenines 3 and 4, use of phase-transfer conditions altered this to ca. 1: 2. Reduction followed by N-prenylation of the resulting secondary amines gave C, N-dialkylated products. The derived separable diastereoisomeric (-)-and (+)-Barton esters 19a and 19b were then converted into (-)-debromoflustramine B and (+)-ent-debromoflustramine B, respectively. A novel reaction involving oxygen and the carbanion derived from Barton ester 19b led to (+)-ent-debromoflustramide B. Treatment of N-8-prenylated Witkop's pyrroloindole 5 with Lewis acid (BF3 center dot Et2O) uncovered a new clean intramolecular cyclisation involving the prenyl unit. (C) 2007 Elsevier Ltd. All rights reserved.

引用

页码：10211 / 10225

页数：15

共 43 条

[1]

ANTHONI U, 1999, ALKALOIDS CHEM BIOL, P113

[2] Enantioselective organocatalytic construction of pyrroloindolines by a cascade addition-cyclization strategy: Synthesis of (-)-flustramine B [J].

Austin, JF ;

Kim, SG ;

Sinz, CJ ;

Xiao, WJ ;

MacMillan, DWC .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) :5482-5487

[3] THE INVENTION OF RADICAL REACTIONS .18. DECARBOXYLATIVE RADICAL-ADDITION TO ARSENIC, ANTIMONY, AND BISMUTH PHENYLSULFIDES - A NOVEL SYNTHESIS OF NOR-ALCOHOLS FROM CARBOXYLIC-ACIDS [J].

BARTON, DHR ;

BRIDON, D ;

ZARD, SZ .

TETRAHEDRON, 1989, 45 (09) :2615-2626

[4] THE INVENTION OF RADICAL REACTIONS .25. A CONVENIENT METHOD FOR THE SYNTHESIS OF THE ACYL DERIVATIVES OF N-HYDROXYPYRIDINE-2-THIONE [J].

BARTON, DHR ;

SAMADI, M .

TETRAHEDRON, 1992, 48 (35) :7083-7090

[5] A CONVENIENT HIGH YIELDING SYNTHESIS OF NOR-ALCOHOLS FROM CARBOXYLIC-ACIDS [J].

BARTON, DHR ;

BRIDON, D ;

ZARD, SZ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (16) :1066-1068

[6] THE INVENTION OF NEW RADICAL CHAIN REACTIONS .8. RADICAL CHEMISTRY OF THIOHYDROXAMIC ESTERS - A NEW METHOD FOR THE GENERATION OF CARBON RADICALS FROM CARBOXYLIC-ACIDS [J].

BARTON, DHR ;

CRICH, D ;

MOTHERWELL, WB .

TETRAHEDRON, 1985, 41 (19) :3901-3924

[7] MANIPULATION OF THE CARBOXYL GROUPS OF ALPHA-AMINO-ACIDS AND PEPTIDES USING RADICAL CHEMISTRY BASED ON ESTERS OF N-HYDROXY-2-THIOPYRIDONE [J].

BARTON, DHR ;

HERVE, Y ;

POTIER, P ;

THIERRY, J .

TETRAHEDRON, 1988, 44 (17) :5479-5486

[8] HOMOGENEOUS CATALYTIC-OXIDATION OF SECONDARY ALCOHOLS TO KETONES BY MOLECULAR-OXYGEN UNDER MILD CONDITIONS [J].

BLACKBURN, TF ;

SCHWARTZ, J .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (05) :157-158

[9] BIOACTIVE ALKALOIDS .4. RESULTS OF RECENT INVESTIGATIONS WITH COLCHICINE AND PHYSOSTIGMINE [J].

BROSSI, A .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (09) :2311-2319

[10] SELECTIVE REDUCTIONS .V. PARTIAL RED1CTION OF TERTIARY AMIDES BY LITHIUM DI- + TRIETHOXYALUMINOHYDRIDES-NEW ALDEHYDE SYNTHESIS VIA DIMETHYLAMIDES [J].

BROWN, HC ;

TSUKAMOTO, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (06) :1089-&

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