Total Synthesis of Enantiopure Phalarine via a Stereospecific Pictet-Spengler Reaction: Traceless Transfer of Chirality from L-Tryptophan

被引：62

作者：

Trzupek, John D. ^{[1
]}

Lee, Dongjoo ^{[1
]}

Crowley, Brendan M. ^{[1
]}

Marathias, Vasilios M. ^{[2
]}

Danishefsky, Samuel J. ^{[1
,3
]}

机构：

[1] Sloan Kettering Inst Canc Res, Bioorgan Chem Lab, New York, NY 10065 USA

[2] Pfizer Global Res & Dev, Cambridge, MA 02140 USA

[3] Columbia Univ, Dept Chem, New York, NY 10027 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 24期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

PROTEASOME INHIBITORS TMC-95A; ELECTROPHILIC SUBSTITUTION; AMINO-ACIDS; 2,3-DISUBSTITUTED INDOLES; 3-SUBSTITUTED INDOLES; INTERNAL ALKYNES; TRYPROSTATIN B; REARRANGEMENT; DERIVATIVES; GENERATION;

D O I：

10.1021/ja1030968

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An appropriately constructed 2-substituted derivative of L-tryptophan undergoes conversion to a prephalarine structure in a single step. The reaction occurs in a diastereoselective fashion, leading shortly thereafter to the naturally occurring version of the alkaloid phalarine.

引用

页码：8506 / 8512

页数：7

共 40 条

[1]

Anderton N, 1999, PHYTOCHEMISTRY, V51, P153, DOI 10.1016/S0031-9422(98)00725-0

[2] 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

[3] Tandem radical decarboxylation-oxidation of amino acids:: A mild and efficient method for the generation of N-acyliminium ions and their nucleophilic trapping [J].

Boto, A ;

Hernández, R ;

Suárez, E .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (16) :4930-4937

[4] Studies toward the total synthesis of phalarine: a survey of some biomimetic possibilities [J].

Chan, Collin ;

Li, Chaomin ;

Zhang, Fei ;

Danishefsky, Samuel J. .

TETRAHEDRON LETTERS, 2006, 47 (28) :4839-4841

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

COX, ED ;

COOK, JM .

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

[6] APPROACHES TO THE SYNTHESIS OF THE MITOMYCINS - A ROUTE TO THE MITOSANES INVOLVING ACTIVATED CYCLOPROPANES [J].

DANISHEFSKY, S ;

REGAN, J ;

DOEHNER, R .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (26) :5255-5261

[7] ROUTE TO FUNCTIONALIZED MITOSANES [J].

DANISHEFSKY, S ;

DOEHNER, R .

TETRAHEDRON LETTERS, 1977, (35) :3031-3034

[8]

DANISHEFSKY SJ, 1995, SYNLETT, P475

[9] Total synthesis of 5-N-acetylardeemin and amauromine:: Practical routes to potential MDR reversal agents [J].

Depew, KM ;

Marsden, SP ;

Zatorska, D ;

Zatorski, A ;

Bornmann, WG ;

Danishefsky, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (51) :11953-11963

[10] Total synthesis of tryprostatin B: Generation of a nucleophilic prenylating species from a prenylstannane [J].

Depew, KM ;

Danishefsky, SJ ;

Rosen, N ;

SeppLorenzino, L .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (49) :12463-12464

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