Biomimetic Total Synthesis of Angelicoin A and B via a Palladium-Catalyzed Decarboxylative Prenylation-Aromatization Sequence

被引：34

作者：

Anderson, Katie ^{[1
]}

Calo, Frederick ^{[1
]}

Pfaffeneder, Toni ^{[1
]}

White, Andrew J. P. ^{[1
]}

Barrett, Anthony G. M. ^{[1
]}

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 21期

基金：

英国工程与自然科学研究理事会;

关键词：

CONVERGENT SYNTHESIS; NATURAL-PRODUCTS; DERIVATIVES; ALLYLATION; COMPLEXES; LACTONES; ACIDS;

D O I：

10.1021/ol202320m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Five-step total syntheses of angelicoin A and B from 2,2,6-trimethyl-4-dioxinone are reported using late stage biomimetic aromatization reactions via diketo-dioxinones as intermediates. In addition, with angelicoin A, this aromatization was coupled with a palladium-catalyzed decarboxylative prenylation in a one-pot sequence as the key step.

引用

页码：5748 / 5750

页数：3

共 34 条

[1] A SIMPLE SYNTHESIS OF GAMMA-KETO AND DELTA-KETO ALPHA-AMINO-ACID DERIVATIVES [J].

AUBRY, N ;

PLANTE, R ;

DEZIEL, R .

TETRAHEDRON LETTERS, 1990, 31 (44) :6311-6312

[2] CONVENIENT SYNTHESES OF ALKYL BETA-RESORCYLATE DERIVATIVES [J].

BARRETT, AGM ;

MORRIS, TM ;

BARTON, DHR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (10) :2272-2277

[3] Studies on the resorcylates: biomimetic total syntheses of (+)-montagnetol and (+)-erythrin [J].

Basset, Jean-Francois ;

Leslie, Colin ;

Hamprecht, Dieter ;

White, Andrew J. P. ;

Barrett, Anthony G. M. .

TETRAHEDRON LETTERS, 2010, 51 (05) :783-785

[4] The enantioselective Tsuji allylation [J].

Behenna, DC ;

Stoltz, BM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15044-15045

[5]

BIRCH A J, 1957, Fortschr Chem Org Naturst, V14, P186

[6] STUDIES IN RELATION TO BIOSYNTHESIS .1. SOME POSSIBLE ROUTES TO DERIVATIVES OF ORCINOL AND PHLOROGLUCINOL [J].

BIRCH, AJ ;

DONOVAN, FW .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1953, 6 (04) :360-368

[7]

Boeckman R.H., 1988, TOTAL SYNTHESIS NATU, V7, P1

[8] A NEW, HIGHLY EFFICIENT, SELECTIVE METHODOLOGY FOR FORMATION OF MEDIUM-RING AND MACROCYCLIC LACTONES VIA INTRAMOLECULAR KETENE TRAPPING - AN APPLICATION TO A CONVERGENT SYNTHESIS OF (-)-KROMYCIN [J].

BOECKMAN, RK ;

PRUITT, JR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (21) :8286-8288

[9] SYNTHETIC STUDIES DIRECTED TOWARD THE NATURALLY-OCCURRING ACYL TETRAMIC ACIDS .1. CONVERGENT TOTAL SYNTHESIS OF (+/-)-TIRANDAMYCIN-A [J].

BOECKMAN, RK ;

STARRETT, JE ;

NICKELL, DG ;

SUM, PE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (18) :5549-5559

[10] STUDIES DIRECTED TOWARD THE SYNTHESIS OF NATURALLY-OCCURRING ACYLTETRAMIC ACIDS .2. PREPARATION OF THE MACROCYCLIC SUBUNIT OF IKARUGAMYCIN [J].

BOECKMAN, RK ;

PERNI, RB .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (26) :5486-5490

← 1 2 3 4 →