A stereoselective, Sm(II)-mediated approach to decorated cis-hydrindanes: synthetic studies on faurinone and pleuromutilin

被引：24

作者：

Findley, Thomas J. K. ^{[1
]}

Sucunza, David ^{[1
]}

Miller, Laura C. ^{[1
]}

Helm, Matthew D. ^{[1
]}

Helliwell, Madeleine ^{[1
]}

Davies, David T. ^{[2
]}

Procter, David J. ^{[1
]}

机构：

[1] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England

[2] GlaxoSmithKline, Stevenage SG1 2NY, Herts, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2011年 / 9卷 / 07期

基金：

英国工程与自然科学研究理事会;

关键词：

ANTI-MESO-ACETYLMETHYLDIVINYLCYCLOPENTANE; METATHESIS REACTIONS; SAMARIUM DIIODIDE; CONCISE SYNTHESIS; RADICALS; REAGENTS; SKELETON; ACCESS; SMI2;

D O I：

10.1039/c0ob01086c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cis-hydrindane motif is found in a number of natural products that display important biological activity. A flexible, stereoselective approach to the framework has been developed that features highly diastereoselective, SmI2-mediated cyclisations. The strategy has been exploited in the first synthesis of the proposed structure of faurinone and an approach to the skeleton of the antibacterial natural product, pleuromutilin.

引用

页码：2433 / 2451

页数：19

共 60 条

[1]

ABE N, 1968, TETRAHEDRON LETT, P1993

[2]

AOKI K, 1993, CHEM PHARM BULL, V41, P994

[3] Enantioselective total synthesis of 3-epi-ottelione A [J].

Araki, H ;

Inoue, M ;

Katoh, T .

SYNLETT, 2003, (15) :2401-2403

[4] A concise synthesis of the tricyclic skeleton of pleuromutilin and a new approach to cycloheptenes [J].

Bacqué, E ;

Pautrat, F ;

Zard, SZ .

ORGANIC LETTERS, 2003, 5 (03) :325-328

[5] Studies on the chemoselectivity and diastereoselectivity of samarium(II) iodide mediated transformations of carbohydrate derived ω-halo-α,β-unsaturated esters [J].

Bennett, SM ;

Biboutou, RK ;

Zhou, ZH ;

Pion, R .

TETRAHEDRON, 1998, 54 (19) :4761-4786

[6] SYNTHETIC STUDIES DIRECTED TOWARD NATURALLY-OCCURRING CYCLOOCTANOIDS .2. A STEREOCONTROLLED ASSEMBLY OF (+/-)-PLEUROMUTILIN VIA A REMARKABLE STERICALLY DEMANDING OXY-COPE REARRANGEMENT [J].

BOECKMAN, RK ;

SPRINGER, DM ;

ALESSI, TR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (21) :8284-8286

[7]

BOECKMAN RKJ, 1991, STRATEGIES TACTICS O, V3

[8] A STRUCTURE OF FAURINONE, A SESQUITERPENE KETONE ISOLATED FROM VALERIANA-OFFICINALIS [J].

BOS, R ;

HENDRIKS, H ;

KLOOSTERMAN, J ;

SIPMA, G .

PHYTOCHEMISTRY, 1983, 22 (06) :1505-1506

[9] 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

[10] A short and convenient access to a trans-hydrindane unit from the anti-meso-acetylmethyldivinylcyclopentane via a radical pathway [J].

Chapelon, AS ;

Ollivier, C ;

Santelli, M .

TETRAHEDRON LETTERS, 2006, 47 (16) :2747-2750

← 1 2 3 4 5 6 →