Total synthesis of (+)-ambruticin S: Probing the pharmacophoric subunit

Journal of Organic Chemistry

Volumn 75, Issue 16, 2010, Pages 5601-5618

  Hanessian, Stephen ^a   Focken, Thilo ^a   Mi, Xueling ^a   Oza, Rupal ^a   Chen, Bin ^a   Ritson, Dougal ^a   Beaudegnies, Renaud ^b  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

^b SYNGENTA CROP PROTECTION AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

6-ENDO-TRIG; ANTI-FUNGAL; CYCLOPROPANATION; DIASTEREOSELECTIVE; DIHYDROPYRAN; ENANTIOSELECTIVE SYNTHESIS; GLUCOPYRANOSIDE; GLYCIDOL; LEWIS ACID; NATURAL PRODUCTS; STEREOGENIC CENTERS; TARGET MOLECULE; TOTAL SYNTHESIS;

ESTERIFICATION; ESTERS; SYNTHESIS (CHEMICAL);

CYCLIZATION;

(2,6) 6 ETHYL 2 (5 IODO 4 METHYLPENT 2 EN 2 YL) 5 METHYL 3,6 DIHYDRO 2H PYRAN; 1 (BENZYLOXY) 2 [(TERT BUTYLDIMETHYLSILYL)OXY] 5 METHYLOCT 5 EN 4 ONE; 1 (BENZYLOXY) 3 (2 (PENT 2 EN 2 YL) 1,3 DITHIAN 2 YL)PROPAN 2 OL; 1 (BENZYLOXY) 5 METHYLOCT 5 ENE 2,4 DIOL; 1 [(2,6) 6 ETHYL 5 METHYL 3,6 DIHYDRO 2H PYRAN 2 YL]ETHANONE; 1,3 DIMETHYL 1,3,2 DIAZAPHOSPHOLIDINE 2 OXIDE; 2 (BENZYLOXYMETHYL) 6 ETHYL 5 METHYL 3,6 DIHYDRO 2H PYRAN; 2 (PENT 2 EN 2 YL) 1,3 DITHIANE; 2 [3 [(TERT BUTYLDIMETHYLSILYL)OXY] 2 METHYLPROPYL] 1,3 DIMETHYL 1,3,2 DIAZAPHOSPHOLIDINE 2 OXIDE; 2 [4 [(2,6) 6 ETHYL 5 METHYL 3,6 DIHYDRO 2H PYRAN 2 YL] 2 METHYLPENT 3 EN 1 YL] 1,3 DIMETHYL 1,3,2 DIAZAPHOSPHOLIDINE 2 OXIDE; 3,4 BIS(BENZYLOXY) 2 METHOXY 6 VINYL TETRAHYDRO 2H PRYAN; 3,4 BIS(BENZYLOXY) 6 (2 (BENZYLOXY)ETHYL) TETRAHYDROPYRAN 2 ONE; 4 [(2,6) 6 ETHYL 5 METHYL 3,6 DIHYDRO 2H PYRAN 2 YL] 2 METHYLPENT 3 EN 1 OL; [(2,6) 6 ETHYL 5 METHYL 3,6 DIHYDRO 2H PYRAN 2 YL]METHANOL; AMBRUTICIN; AMBRUTICIN S; ANTIFUNGAL AGENT; METHYL 4,6 DICHLORO 4,6 DIDEOXY ALPHA DEXTRO GLUCOPYRANOSIDE; METHYL 6 C (1 PROPENYL) 4,6 DIDEOXY 2,3 DI O BENZYL ALPHA DEXTRO GLUCOPYRANOSIDE; METHYL 6 C (2 PROPENYL) 4,6 DIDEOXY 2,3 DI O BENZYL ALPHA DEXTRO GLUCOPYRANOSIDE; METHYL 6 C (BENZYLOXYMETHYL) 4,6 DIDEOXY 2,3 DI O BENZYL ALPHA DEXTRO GLUCOPYRANOSIDE; METHYL 6 C (HYDROXYMETHYL) 4,6 DIDEOXY 2,3 DI O BENZYL ALPHA DEXTRO GLUCOPYRANOSIDE; METHYL 6 CHLORO 4,6 DIDEOXY 2,3 DI O BENZYL ALPHA DEXTRO GLUCOPYRANOSIDE; METHYL 6 CHLORO 4,6 DIDEOXY ALPHA DEXTRO GLUCOPYRANOSIDE; METHYL 6 CYANO 4,6 DIDEOXY 2,3 DI O BENZYL ALPHA DEXTRO GLUCOPYRANOSIDE; NATURAL PRODUCT; TERT BUTYL 2 [(1,4) 5 [(2,6) 6 ETHYL 5 METHYL 3,6 DIHYDRO 2H PYRAN 2 YL] 3 METHYLHEXA 1,4 DIEN 1 YL] 3 METHYLCYCLOPROPANECARBOXYLATE; TERT BUTYL 2 [2 [(3A,7A) 1,3 DIMETHYL 2 OXIDOHEXAHYDRO 1H BENZO[D][1,3,2]DIAZAPHOSPHOL 2(3H) YL]VINYL] 3 METHYLCYCLOPROPANECARBOXYLATE; TERT BUTYL 2 FORMYL 3 METHYLCYCLOPROPANECARBOXYLATE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIFUNGAL ACTIVITY; ARTICLE; CONTROLLED STUDY; CRYSTAL STRUCTURE; CYCLIZATION; CYCLOPROPANATION; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOSELECTIVITY; GLYCOSYLATION; OLEFINATION; PHARMACOPHORE;

ANTIFUNGAL AGENTS; BIOLOGICAL FACTORS; CYCLIZATION; GLYCOSYLATION; MOLECULAR CONFORMATION; PYRANS; STEREOISOMERISM;

EID: 77955666610     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100956v     Document Type: Article

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