Syntheses of (-)-TAN-2483A, (-)-massarilactone B, and the fusidilactone B ring system.: Revision of the structures of and syntheses of (±)-Waol A (FD-211) and (±)-Waol B (FD-212)

被引：27

作者：

Gao, XL ^{[1
]}

Snider, BB ^{[1
]}

机构：

[1] Brandeis Univ, Dept Chem, Waltham, MA 02454 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 17期

关键词：

D O I：

10.1021/jo0358628

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The structure of waol A has been revised from 1 to 6, the vinylogue of TAN-2483A (5). Aldol reaction of hydroxybutanolides 13b,c with 2,4-hexadienal affords 12b,c, which are subjected to iodoetherification with bis(sym-collidine)IPF6 to provide 11b(c). Treatment with Et3N in CH2Cl2 completes the three-step syntheses of TAN-2483A (5) and waol A (6). Aldol reaction of hydroxybutanolide 31 with 2,4-hexadienal affords 32, which is subjected to iodoetherification to provide 34, which in turn is treated with Bu3SnCl, NaBH3CN, and oxygen to provide diol 60. Further elaboration completes the first syntheses of massarilactone B (7) and the fusidilactone B (9) ring system.

引用

收藏

页码：5517 / 5527

页数：11

相关论文

共 40 条

[1] A highly chemoselective, diastereoselective, and regioselective epoxidation of chiral allylic alcohols with hydrogen peroxide, catalyzed by sandwich-type polyoxometalates:: Enhancement of reactivity and control of selectivity by the hydroxy group through metal-alcoholate bonding [J].

Adam, W ;

Alsters, PL ;

Neumann, R ;

Saha-Möller, CR ;

Sloboda-Rozner, D ;

Zhang, R .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (05) :1721-1728

[2] NMR-SPECTRUM OF A CONJUGATED ALDEHYDE - SORBALDEHYDE [J].

ALBRIKTS.P ;

HARRIS, RK .

ACTA CHEMICA SCANDINAVICA, 1973, 27 (10) :3993-4000

[3] METABOLITES OF THE HIGHER FUNGI .19. SERPENONE, 3-METHOXY-4-METHYL-5-PROP-1-ENYLFURAN-2(5H)-ONE, A NEW GAMMA-BUTYROLACTONE FROM THE FUNGUS HYPOXYLON-SERPENS (BARRONS STRAIN) (PERSOON EX FRIES)KICKX [J].

ANDERSON, JR ;

EDWARDS, RL ;

WHALLEY, AJS .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (01) :215-221

[4] SYNTHESIS OF (+/-)-NOR-STEREPOLIDE [J].

ARAI, Y ;

TAKEDA, K ;

MASUDA, K ;

KOIZUMI, T .

CHEMISTRY LETTERS, 1985, (10) :1531-1534

[5] MICROBIAL METABOLITES .11. TOTAL SYNTHESIS AND ABSOLUTE-CONFIGURATION OF (S)-CARLOSIC ACID (4-BUTYRYL-2,5-DIHYDRO-3-HYDROXY-5-OXO-FURAN-2-ACETIC ACID) AND CONVERSION OF (R)-5-METHYLTETRONIC ACID INTO (R)-CAROLIC ACID (3,4-DIHYDRO-8-METHYLFURO[3,4-B]OXEPIN-5,6(2H,8H)-DI-ONE) [J].

BLOOMER, JL ;

KAPPLER, FE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (14) :1485-1491

[6] NATURALLY OCCURRING LACTONES AND LACTAMES .2. ABSOLUTE CONFIGURATION OF GAMMA-METHYLTETRONIC ACID CAROLINIC ACID AND CAROLIC ACID [J].

BOLL, PM ;

SORENSEN, E ;

BALIEU, E .

ACTA CHEMICA SCANDINAVICA, 1968, 22 (10) :3251-&

[7] Preparation of oxepanes, oxepenes, and oxocanes by iodoetherification using bis(sym-collidine)iodine(I) hexafluorophosphate as electrophile [J].

Brunel, Y ;

Rousseau, G .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (17) :5793-5800

[8] SYNTHESIS OF OPTICALLY-ACTIVE SILYL PROTECTED CYANOHYDRINS [J].

BRUSSEE, J ;

LOOS, WT ;

KRUSE, CG ;

VANDERGEN, A .

TETRAHEDRON, 1990, 46 (03) :979-986

[9] MODELING CHEMICAL-REACTIVITY .7. THE EFFECT OF A CHANGE IN RATE-LIMITING STEP ON THE STEREOSELECTIVITY OF ELECTROPHILIC ADDITION TO ALLYLIC ALCOHOLS AND RELATED CHIRAL ALKENES [J].

CHAMBERLIN, AR ;

MULHOLLAND, RL ;

KAHN, SD ;

HEHRE, WJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (03) :672-677

[10] IODOCYCLIZATION OF ALLYLIC ALCOHOL DERIVATIVES CONTAINING INTERNAL NUCLEOPHILES - CONTROL OF STEREOSELECTIVITY BY SUBSTITUENTS IN THE ACYCLIC PRECURSORS [J].

CHAMBERLIN, AR ;

DEZUBE, M ;

DUSSAULT, P ;

MCMILLS, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (18) :5819-5825

← 1 2 3 4 →