Stereoselective synthesis of both tetrahydropyran rings of the antitumor macrolide, (-)-lasonolide A

Journal of Organic Chemistry

Volumn 77, Issue 5, 2012, Pages 2559-2565

  Ghosh, Arun K ^a   Ren, Guo Bao ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTI-TUMORS; FUNCTIONALIZED; HETERO DIELS-ALDER REACTION; MACROLIDES; OPENING REACTIONS; QUATERNARY STEREOCENTERS; REGIO-SELECTIVE; STEREO-SELECTIVE; STEREOSELECTIVE SYNTHESIS; TETRAHYDROPYRAN;

DRUG PRODUCTS; STEREOCHEMISTRY;

STEREOSELECTIVITY;

1 PHENYL 5 [[3 [(1 PHENYL 1H TETRAZOL 5 YL)SULFONYL]PROPYL]THIO] 1H TETRAZOLE; 2 [( BENZYLOXY)METHYL] 6 [2 [(TERT BUTYLDIMETHYLSILYL)OXY]ETHYL] 3 METHYLTETRAHYDRO 2H PYRAN 4 OL; 2 [(BENZYLOXY)METHYL) 6 [2 [(TERT BUTYLDIMETHYLSILYL)OXY]ETHYL] 3 METHYLTETRAHYDRO 2H PYRAN 4 OL; 2 [(BENZYLOXY)METHYL] 6 [2 [(TERT BUTYLDIMETHYLSILYL)OXY]ETHYL] 3 METHYLDIHYDRO 2H PYRAN 4 (3H)ONE; 2 [2,2,4A TRIMETHYL 7 [4 [(1 PHENYL 1H TETRAZOL 5 YL)SULFONYL]BUT 1 EN 1 YL]HEXAHYDROPYRANO[4,3 D][1,3]DIOXIN 5 YL]ETHANOL; 2 [6 [(BENZYLOXY)METHYL] 4 [(TERT BUTYLDIMETHYLSILYL)OXY] 5 METHYLTETRAHYDRO 2H PYRAN 2 YL]ETHANOL; 6 [(BENZYLOXY)METHYL] 2 [2 [ (TERT BUTYLDIMETHYLSILYL)OXY]ETHYL] 3 (HYDROXYMETHYL) 3 METHYLTETRAHYDRO 2H PYRAN 4 OL; [2 [6 (BENZYLOXYMETHYL) 4 (TRIMETHYLSILYLOXY) 5,6 DIHYDRO 2H PYRAN 2 YL]ETHOXY](TERT BUTYL)DIMETHYLSILANE; [2 [6 [(BENZYLOXY)METHYL] 5 METHYL 5,6 DIHYDRO 2H PYRAN 2 YL]ETHOXY](TERT BUTYL)DIMETHYLSILANE; [2 [6 [BENZYLOXYMETHYL) 5 METHYL 4 (TRIETHYLSILYLOXY) 5,6 DIHYDRO 2H PYRAN 2 YL]ETHOXY](TERT BUTYL)DIMETHYLSILANE; [4 [(TERT BUTYLDIMETHYLSILYL)OXY] 6 [4 [(TERTBUTYLDIMETHYLSILYL)BUT 2 EN 1 YL] 3 METHYLTETRAHYDRO 2H PYRAN 2 YL]METHANOL; [5 [2 [(TERT BUTYLDIMETHYLSILYL)OXY]ETHYL] 2,2,4A TRIMETHYLHEXAHYDROPYRANO[4,3 D][1,3]DIOXIN 7 YL] METHANOL; ANTINEOPLASTIC AGENT; EPOXIDE; ETHYL 4 [6 [(BENZYLOXY)METHYL] 4 [(TERTBUTYLDIMETHYLSILYL)OXY] 5 METHYLTETRAHYDRO 2H PYRAN 2 YL)BUT 2 ENOATE; ETHYL 6 [(BENZYLOXY)METHYL] 2 [2 [(TERTBUTYLDIMETHYLSILYL)OXY]ETHYL] 3 METHYL 4 OXOTETRAHYDRO 2H PYRAN 3 CARBOXYLATE; LASONOLIDE A; MACROLIDE; TETRAHYDROPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; DIELS ALDER REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; EPOXIDATION; RING OPENING; STEREOCHEMISTRY;

ANTINEOPLASTIC AGENTS; MACROLIDES; MOLECULAR STRUCTURE; PYRANS; STEREOISOMERISM;

EID: 84857848358     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo202631e     Document Type: Article

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