Total synthesis of (±)-trichodermamide B and of a putative biosynthetic precursor to aspergillazine A using an oxaza-Cope rearrangement

被引：39

作者：

Lu, Chong-Dao ^{[2
]}

Zakarian, Armen ^{[1
]}

机构：

[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

[2] Florida State Univ, Dept Chem & Biochem, Tallahassee, FL 32306 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 36期

关键词：

heterocycles; natural products; peptides; sigmatropic rearrangement; total synthesis;

D O I：

10.1002/anie.200801652

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Coping with tandem reactions: The total synthesis of marine fungal metabolite, trichodermamide B, is accomplished using a tandem nitrosation/oxaza-Cope rearrangement as the key step to establish the characteristic heterocyclic ring system of the natural product. Preparation of the putative biosynthetic precursor of aspergillazine A provides further insight into the possible biosynthetic pathway to aspergillazines. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：6829 / 6831

页数：3

共 25 条

[1]

Al-Qawasmeh RA, 1999, CHEM LETT, P541

[2] Aspergillazines A-E:: novel heterocyclic dipeptides from an Australian strain of Aspergillus unilateralis [J].

Capon, RJ ;

Ratnayake, R ;

Stewart, M ;

Lacey, E ;

Tennant, S ;

Gill, JH .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (01) :123-129

[3] 1,3-TRANSPOSITION OF PRIMARY ALLYLIC ALCOHOLS - NEW APPLICATION OF SELENOXIDE CHEMISTRY [J].

CLIVE, DLJ ;

CHITTATTU, G ;

CURTIS, NJ ;

MENCHEN, SM .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (17) :770-771

[4] THE CYCLOADDITION OF ALPHA-NITROSOSTYRENES TO OLEFINS - INVESTIGATIONS OF THE SCOPE AND MECHANISM OF THE REACTION [J].

DAVIES, DE ;

GILCHRIST, TL ;

ROBERTS, TG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (06) :1275-1281

[5] Tandem oxime formation - epoxide ring opening sequences for the preparation of oxazines related to the trichodermamides [J].

Donald, James R. ;

Edwards, Michael G. ;

Taylor, Richard J. K. .

TETRAHEDRON LETTERS, 2007, 48 (30) :5201-5204

[6] Trichodermamides A and B, cytotoxic modified Dipeptides from the marine-derived fungus Trichoderma virens [J].

Garo, E ;

Starks, CM ;

Jensen, PR ;

Fenical, W ;

Lobkovsky, E ;

Clardy, J .

JOURNAL OF NATURAL PRODUCTS, 2003, 66 (03) :423-426

[7]

GILCHRIST TL, 1978, J CHEM SOC CHEM COMM, P847

[8] NITROSO-ALKENES AND NITROSO-ALKYNES [J].

GILCHRIST, TL .

CHEMICAL SOCIETY REVIEWS, 1983, 12 (01) :53-73

[9] ETHYL 3-BROMO-2-HYDROXYIMINOPROPANOATE, A REAGENT FOR THE PREPARATION OF ETHYL-ESTERS OF ALPHA-AMINO-ACIDS [J].

GILCHRIST, TL ;

LINGHAM, DA ;

ROBERTS, TG .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (23) :1089-1090

[10] ORGANOSELENIUM CHEMISTRY - FACILE ONE-STEP SYNTHESIS OF ALKYL ARYL SELENIDES FROM ALCOHOLS [J].

GRIECO, PA ;

GILMAN, S ;

NISHIZAWA, M .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (08) :1485-1486

← 1 2 3 →