Enantioselective syntheses of tremulenediol A and tremulenolide A

被引：49

作者：

Ashfeld, BL ^{[1
]}

Martin, SF ^{[1
]}

机构：

[1] Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 20期

关键词：

D O I：

10.1021/ol051945u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

graph An enantioselective entry to the skeleton of the tremulane sesquiterpenes is described. The approach features a series of efficient transition metal-catalyzed reactions commencing with an enantioselective rhodium(ll)-catalyzed intramolecular cyclopropa nation followed by a regioselective allylic alkylation and a diastereoselective rhodium(l)-catalyzed [5 + 2] cycloaddition. This strategy was applied to the first enantioselective syntheses of tremulenediol A and tremulenolide A.

引用

页码：4535 / 4537

页数：3

共 11 条

[1] NOVEL CONVERSION OF EPOXIDES TO ONE-CARBON HOMOLOGATED ALLYLIC ALCOHOLS BY DIMETHYLSULFONIUM METHYLIDE [J].

ALCARAZ, L ;

HARNETT, JJ ;

MIOSKOWSKI, C ;

MARTEL, JP ;

LEGALL, T ;

SHIN, DS ;

FALCK, JR .

TETRAHEDRON LETTERS, 1994, 35 (30) :5449-5452

[2] [Rh(CO)2Cl]2-catalyzed domino reactions involving allylic substitution and subsequent carbocyclization reactions [J].

Ashfeld, BL ;

Miller, KA ;

Smith, AJ ;

Tran, K ;

Martin, SF .

ORGANIC LETTERS, 2005, 7 (08) :1661-1663

[3] Direct, stereoselective substitution in [Rh(CO)2CI]2-catalyzed allylic alkylations of unsymmetrical substrates [J].

Ashfeld, BL ;

Miller, KA ;

Martin, SF .

ORGANIC LETTERS, 2004, 6 (08) :1321-1324

[4] THE TREMULANES, A NEW GROUP OF SESQUITERPENES FROM THE ASPEN ROTTING FUNGUS PHELLINUS-TREMULAE [J].

AYER, WA ;

CRUZ, ER .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (26) :7529-7534

[5] Highly selective silver(I) oxide mediated monoprotection of symmetrical diols [J].

Bouzide, A ;

Sauve, G .

TETRAHEDRON LETTERS, 1997, 38 (34) :5945-5948

[6] EFFICIENT SYNTHESIS AND INTRAMOLECULAR CYCLOPROPANATION OF UNSATURATED DIAZOACETIC ESTERS [J].

COREY, EJ ;

MYERS, AG .

TETRAHEDRON LETTERS, 1984, 25 (33) :3559-3562

[7] Total synthesis of (±)-tremulenolide A and (±)-tremulenediol A via a stereoselective cyclopropanation/cope rearrangement annulation strategy [J].

Davies, HML ;

Doan, BD .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (03) :657-660

[8] ENANTIOSELECTIVE INTRAMOLECULAR CYCLOPROPANATIONS OF ALLYLIC AND HOMOALLYLIC DIAZOACETATES AND DIAZOACETAMIDES USING CHIRAL DIRHODIUM(II) CARBOXAMIDE CATALYSTS [J].

DOYLE, MP ;

AUSTIN, RE ;

BAILEY, AS ;

DWYER, MP ;

DYATKIN, AB ;

KALININ, AV ;

KWAN, MMY ;

LIRAS, S ;

OALMANN, CJ ;

PIETERS, RJ ;

PROTOPOPOVA, MN ;

RAAB, CE ;

ROOS, GHP ;

ZHOU, QL ;

MARTIN, SF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (21) :5763-5775

[9] Conservation of absolute configuration in the acyclic rhodium-catalyzed allylic alkylation reaction:: Evidence for an enyl (σ+π) organorhodium intermediate [J].

Evans, PA ;

Nelson, JD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (22) :5581-5582

[10] Transition metal-catalyzed [5+2] cycloadditions of 2-substituted-1-vinylcyclopropanes: Catalyst control and reversal of regioselectivity [J].

Wender, PA ;

Dyckman, AJ .

ORGANIC LETTERS, 1999, 1 (13) :2089-2092

← 1 2 →