Synthesis of (±)-Merrilactone A and (±)-Anislactone A

被引：55

作者：

Shi, Lei ^{[1
]}

Meyer, Karsten ^{[1
]}

Greaney, Michael F. ^{[1
]}

机构：

[1] Univ Edinburgh, Sch Chem, Edinburgh EH9 3JJ, Midlothian, Scotland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 48期

基金：

英国工程与自然科学研究理事会;

关键词：

diastereoselectivity; natural products; terpenoids; total synthesis; MERRILACTONE-A; ILLICIUM-MERRILLIANUM; ANISLACTONE-B; EFFICIENT; SESQUITERPENE; CYCLIZATIONS; EPOXIDES; ENANTIOMER; REDUCTION; PERICARPS;

D O I：

10.1002/anie.201005156

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A concise synthesis of each of the sesquiterpenoids merrilactone A and anislactone A is described using a common route. Reductive cleavage of an epoxide using TiIII and radical cyclization is used to install the C9 quaternary center at the heart of the BC bicycle (see scheme). Selective lactonization sequences then define regiodivergent pathways to both merrilactone A (formal synthesis) and anislactone A (total synthesis). Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：9250 / 9253

页数：4

共 42 条

[1] First total synthesis of (-)-achilleol B: Reassignment of its relative stereochemistry [J].

Arteaga, Jesus F. ;

Domingo, Victoriano ;

del Moral, Jose F. Quilez ;

Barrero, Alejandro F. .

ORGANIC LETTERS, 2008, 10 (09) :1723-1726

[2] The total synthesis of (±)-merrilactone A [J].

Birman, VB ;

Danishefsky, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (10) :2080-2081

[3] STEREOCONTROLLED SYNTHESIS OF (+/-)-DEBROMOAPLYSIN, (+/-)-APLYSIN, (+/-)-DEBROMOAPLYSINOL, (+/-)-APLYSINOL, AND (+/-)-ISOAPLYSIN [J].

BISWAS, S ;

GHOSH, A ;

VENKATESWARAN, RV .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11) :3498-3502

[4] First comprehensive bakkane approach:: Stereoselective and efficient dichloroketene-based total syntheses of (±)- and (-)-9-acetoxyfukinanolide, (±)- and (+)-bakkenolide A, (-)-bakkenolides III, B, C, H, L, V, and X, (±)- and (-)-homogynolide A, (±)-homogynolide B, and (±)-palmosalide C [J].

Brocksom, TJ ;

Coelho, F ;

Deprés, JP ;

Greene, AE ;

de Lima, MEF ;

Hamelin, O ;

Hartmann, B ;

Kanazawa, AM ;

Wang, YY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (51) :15313-15325

[5] TOTAL SYNTHESIS OF (+/-)-GINKGOLIDE-B [J].

COREY, EJ ;

KANG, M ;

DESAI, MC ;

GHOSH, AK ;

HOUPIS, JN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (02) :649-651

[6] Aluminium(III) trifluoromethanesulfonate as an efficient catalyst for the intramolecular hydroalkoxylation of unactivated olefins:: Experimental and theoretical approaches [J].

Coulombel, Lydie ;

Rajzmann, Michel ;

Pons, Jean-Marc ;

Olivero, Sandra ;

Dunach, Elisabet .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (24) :6356-6365

[7] Reaction of cyclic alpha-hydroxy epoxides with a strong base: A new 1,2-rearrangement, evidence for a carbenoid pathway [J].

Doris, E ;

Dechoux, L ;

Mioskowski, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (51) :12700-12704

[8] Stereocontrolled coupling between aldehydes and conjugated alkenals mediated by TiIII/H2O [J].

Estevez, Rosa E. ;

Oller-Lopez, Juan L. ;

Robles, Rafael ;

Melgarejo, Concepcion R. ;

Gansaeuer, Andreas ;

Cuerva, Juan M. ;

Oltra, J. Enrique .

ORGANIC LETTERS, 2006, 8 (24) :5433-5436

[9] A combined theoretical and experimental study of efficient and fast titanocene-catalyzed 3-exo cyclizations [J].

Friedrich, J ;

Dolg, M ;

Gansäuer, A ;

Geich-Gimbel, D ;

Lauterbach, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (19) :7071-7077

[10] Titanocene catalyzed 4-exo cyclizations:: Mechanism, experiment, catalyst design [J].

Friedrich, Joachim ;

Walczak, Katarzyna ;

Dolg, Michael ;

Piestert, Frederik ;

Lauterbach, Thorsten ;

Worgull, Dennis ;

Gansauer, Andreas .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (05) :1788-1796

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