A Biomimetic Total Synthesis of (+)-Ainsliadimer A

被引：69

作者：

Li, Chao ^{[1
]}

Yu, Xueliang ^{[1
]}

Lei, Xiaoguang ^{[1
,2
]}

机构：

[1] Tianjin Univ, Sch Pharmaceut Sci & Technol, Tianjin 300072, Peoples R China

[2] NIBS, Beijing 102206, Peoples R China

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 19期

关键词：

DIELS-ALDER REACTIONS; SESQUITERPENE LACTONES; NATURAL-PRODUCTS; CATALYSIS; KINETICS; KETONES; DIMER;

D O I：

10.1021/ol101705j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A protecting group free and biomimetic total synthesis of (+)-ainsliadimer A has been accomplished in 14 steps from a-santonin. The synthesis relies on a hydrogen bonding promoted [4 + 2]-hetero-Diels-Alder dimerization to afford the key homodimer intermediate, which demonstrates the feasibility of using nonenzymatic conditions to achieve the proposed biosynthesis.

引用

页码：4284 / 4287

页数：4

共 31 条

[1] STUDIES ON THE SYNTHESES OF SESQUITERPENE LACTONES .11. THE SYNTHESES OF 3-EPIZALUZANIN-C, ZALUZANIN-C, ZALUZANIN-D, AND RELATED-COMPOUNDS 3ALPHA-HYDROXYGUAIA-1(10),4(15),11(13)-TRIENO-12,6ALPHA-LACTONE AND 3ALPHA-HYDROXYGUAIA-4(15),9,11(13)-TRIENO-12,6ALPHA-LACTONE [J].

ANDO, M ;

KUSAKA, H ;

OHARA, H ;

TAKASE, K ;

YAMAOKA, H ;

YANAGI, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (08) :1952-1960

[2] STUDIES ON THE SYNTHESIS OF SESQUITERPENE LACTONES .16. THE SYNTHESES OF 11-BETA,13-DIHYDROKAUNIOLIDE, ESTAFIATIN, ISODEHYDROCOSTUSLACTONE, 2-OXODESOXYLIGUSTRIN, ARBORESCIN, 1,10-EPIARBORESCIN, 11-BETA,13-DIHYDROLUDARTIN, 8-DEOXY-11-BETA,13-DIHYDRORUPICOLIN-B, 8-DEOXYRUPICOLIN-B, 3,4-EPILUDARTIN, LUDARTIN, KAUNIOLIDE, DEHYDROLEUCODIN, AND LEUCODIN [J].

ANDO, M ;

IBAYASHI, K ;

MINAMI, N ;

YOSHIMURA, H ;

NAKAMURA, T ;

ISOGAI, K .

JOURNAL OF NATURAL PRODUCTS, 1994, 57 (04) :433-445

[3] KINETICS OF STEREOMUTATIONS OF (/)-2-DEUTERIO-3,7-DIMETHYL-7-METHOXYMETHYLCYCLOHEPTA-1,3,5-TRIENE - ONE-CENTERED EPIMERIZATION AT C(7) AND [1,5] CARBON MIGRATION WITH RETENTION OF CONFIGURATION IN NORCARADIENE [J].

BALDWIN, JE ;

BROLINE, BM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (14) :4599-4600

[4] PHOTOCHEMICAL TRANSFORMATIONS .1. SOME PRELIMINARY INVESTIGATIONS [J].

BARTON, DHR ;

DEMAYO, P ;

SHAFIQ, M .

JOURNAL OF THE CHEMICAL SOCIETY, 1957, (MAR) :929-935

[5] Biosynthetic and biomimetic electrocyclizations [J].

Beaudry, CM ;

Malerich, JP ;

Trauner, D .

CHEMICAL REVIEWS, 2005, 105 (12) :4757-4778

[6] Synthesis of plagiochiline N from santonin [J].

Blay, G ;

Cardona, L ;

García, B ;

Lahoz, L ;

Pedro, JR .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (23) :7700-7705

[7] Recent advances in biomimetic natural product synthesis [J].

Bulger, Paul G. ;

Bagal, Sharan K. ;

Marquez, Rodolfo .

NATURAL PRODUCT REPORTS, 2008, 25 (02) :254-297

[8] Towards EPC-syntheses of the structural class of cochleamycins and macquarimicins. Part 2: EPC-synthesis of the hydrindene subunit of the macquarimicins [J].

Chrobok, A. ;

Gossinger, E. ;

Kalb, R. ;

Orglmeister, E. ;

Schwaiger, J. .

TETRAHEDRON, 2007, 63 (34) :8326-8335

[9] Investigations into the C-deuteriation of aryl alkyl ketones using urea as a pro-base in the presence of a deuterium donor [J].

Coumbarides, Gregory S. ;

Eames, Jason ;

Suggate, Michael J. ;

Weerasooriya, Neluka .

JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2006, 49 (07) :641-652

[10] Small-molecule H-bond donors in asymmetric catalysis [J].

Doyle, Abigail G. ;

Jacobsen, Eric N. .

CHEMICAL REVIEWS, 2007, 107 (12) :5713-5743

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