Concise, Stereocontrolled Synthesis of the Citrinadin B Core Architecture

被引：27

作者：

Guerrero, Carlos A. ^{[1
]}

Sorensen, Erik J. ^{[1
]}

机构：

[1] Princeton Univ, Dept Chem, Frick Lab, Princeton, NJ 08544 USA

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 19期

基金：

美国国家卫生研究院;

关键词：

TRYPTAMINE DERIVATIVES; CYCLIZATION; TRYPTOPHAN; OXIDATION;

D O I：

10.1021/ol2020362

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise, stereocontrolled synthesis of the citrinadin B core architecture from scalemic, readily available starting materials is disclosed. Highlights include ready access to both cyclic tryptophan tautomer and trans-2,6-disubstituted piperidine fragments, an efficient, stereoretentive mixed Claisen acylation for the coupling of these halves, and further diastereoselective carbonyl addition and oxidative rearrangement for assembly of the core.

引用

页码：5164 / 5167

页数：4

共 31 条

[1] SYNTHESIS OF FUNCTIONALIZED NITROALKANES BY OXIDATION OF OXIMES WITH UREA-HYDROGEN PEROXIDE COMPLEX AND TRIFLUOROACETIC-ANHYDRIDE [J].

BALLINI, R ;

MARCANTONI, E ;

PETRINI, M .

TETRAHEDRON LETTERS, 1992, 33 (33) :4835-4838

[2] ALPHA-LITHIOAMINE SYNTHETIC EQUIVALENTS FROM DIPOLE-STABILIZED CARBANIONS - THE TERT-BOC GROUP AS AN ACTIVATOR FOR ALPHA'-LITHIATION OF CARBAMATES [J].

BEAK, P ;

LEE, WK .

TETRAHEDRON LETTERS, 1989, 30 (10) :1197-1200

[3] ALPHA-LITHIOAMINE SYNTHETIC EQUIVALENTS - SYNTHESES OF DIASTEREOISOMERS FROM BOC DERIVATIVES OF CYCLIC AMINES [J].

BEAK, P ;

LEE, WK .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (05) :1109-1117

[4] CONFORMATIONALLY RESTRICTED AMINO-ACIDS - DIASTEREOSELECTIVE SUBSTITUTION AT THE BETA-POSITION OF L-TRYPTOPHAN [J].

BRUNCKO, M ;

CRICH, D .

TETRAHEDRON LETTERS, 1992, 33 (42) :6251-6254

[5] ENANTIOSPECIFIC SYNTHESIS OF AMINO-ACIDS - PREPARATION OF (R)-ALPHA-METHYLASPARTIC AND (S)-ALPHA-METHYLASPARTIC ACID FROM (S)-TRYPTOPHAN [J].

CHAN, CO ;

CRICH, D ;

NATARAJAN, S .

TETRAHEDRON LETTERS, 1992, 33 (24) :3405-3408

[6] Seebach's Conjunctive Reagent Enables Double Cyclizations [J].

Chandler, Brent D. ;

Roland, Jason T. ;

Li, Yukai ;

Sorensen, Erik J. .

ORGANIC LETTERS, 2010, 12 (12) :2746-2749

[7] COUPLING N-METHYLATED AMINO-ACIDS USING PYBROP AND PYCLOP HALOGENOPHOSPHONIUM SALTS - MECHANISM AND FIELDS OF APPLICATION [J].

COSTE, J ;

FREROT, E ;

JOUIN, P .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (09) :2437-2446

[8]

CRAIG JC, 1971, J ORG CHEM, V36, P3648

[9]

Crich D., 1989, CHEM SOC, P1418

[10]

Crich D., 1997, ACCOUNTS CHEM RES, V40, P151

← 1 2 3 4 →