Efficient construction of the securine A carbon skeleton

被引：20

作者：

Korakas, P ^{[1
]}

Chaffee, S ^{[1
]}

Shotwell, JB ^{[1
]}

Duque, P ^{[1
]}

Wood, JL ^{[1
]}

机构：

[1] Yale Univ, Dept Chem, Sterling Chem Lab, New Haven, CT 06514 USA

来源：

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA | 2004年 / 101卷 / 33期

关键词：

D O I：

10.1073/pnas.0402274101

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

Securamine A is a structurally intriguing alkaloid possessing a pyrroloindole core joined via a modified isoprene subunit to a functionalized imidazole ring. Recent synthetic efforts in this laboratory have resulted in the efficient construction of key lactone 36, which undergoes tandem azide reduction/ring expansion to macrolactam 37. Macrolactam 37 possesses the complete macrocyclic core of securamine A.

引用

页码：12054 / 12057

页数：4

共 26 条

[1] REGENTS AND SYNTHETIC METHODS .60. NEW STEREOCHEMICAL OUTCOMES IN THE CYCLOADDITION OF ACID HALIDES OR EQUIVALENTS TO CINNAMYLIDENEAMINES - A CONCISE NEW APPROACH TO 4-ACETOXYAZETIDIN-2-ONES [J].

AIZPURUA, JM ;

COSSIO, FP ;

LECEA, B ;

PALOMO, C .

TETRAHEDRON LETTERS, 1986, 27 (36) :4359-4362

[2] CHARTELLAMIDE-A AND CHARTELLAMIDE-B, HALOGENATED BETA-LACTAM INDOLE IMIDAZOLE ALKALOIDS FROM THE MARINE BRYOZOAN CHARTELLA-PAPYRACEA [J].

ANTHONI, U ;

BOCK, K ;

CHEVOLOT, L ;

LARSEN, C ;

NIELSEN, PH ;

CHRISTOPHERSEN, C .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (25) :5638-5639

[3] 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

[4] STUDIES OF ENZYME-MEDIATED REACTIONS .13. STEREOCHEMICAL COURSE OF THE FORMATION OF HISTAMINE BY DECARBOXYLATION OF (2S)-HISTIDINE WITH ENZYMES FROM CLOSTRIDIUM-WELCHII AND LACTOBACILLUS 30A [J].

BATTERSBY, AR ;

NICOLETTI, M ;

STAUNTON, J ;

VLEGGAAR, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (01) :43-51

[5] BROMO-SUBSTITUTED PHYSOSTIGMINE ALKALOIDS FROM A MARINE BRYOZOA FLUSTRA-FOLIACEA [J].

CARLE, JS ;

CHRISTOPHERSEN, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (14) :4012-4013

[6] MARINE ALKALOIDS .2. BROMO ALKALOIDS FROM THE MARINE BRYOZOAN FLUSTRA-FOLIACEA - ISOLATION AND STRUCTURE ELUCIDATION [J].

CARLE, JS ;

CHRISTOPHERSEN, C .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (09) :1586-1589

[7]

CHAFFEE SC, 1999, THESIS YALE U NEW HA

[8] Asymmetric dihydroxylation enables rapid construction of chiral dendrimers based on 1,2-diols [J].

Chang, HT ;

Chen, CT ;

Kondo, T ;

Siuzdak, G ;

Sharpless, KB .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (02) :182-186

[9] 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

[10] STUDIES IN STEREOCHEMISTRY .1. THE STEREOSPECIFIC WAGNER-MEERWEIN REARRANGEMENT OF THE ISOMERS OF 3-PHENYL-2-BUTANOL [J].

CRAM, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (12) :3863-3870

← 1 2 3 →