Relative stereochemical determination and synthesis of the C17-C25 δ-lactone fragment of hemicalide

Journal of Organic Chemistry

Volumn 78, Issue 3, 2013, Pages 855-864

  Fleury, Etienne ^a   Sorin, Geoffroy ^a   Prost, Elise ^a   Pancrazi, Ange ^a   Sautel, François ^b   Massiot, Georges ^b   Lannou, Marie Isabelle ^a   Ardisson, Janick ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

^b INSTITUT DE RECHERCHE PIERRE FABRE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE ALLYLATION; COMMON STRATEGY; CONCISE SYNTHESIS; DIASTEREOMERS; DIHYDROXYLATION REACTION; MECHANISM OF ACTION; NATURAL PRODUCTS; NMR ANALYSIS; OLEFINATION; POLYKETIDES; PUTATIVE RELATIVES;

ALDEHYDES; ALLYLATION; ISOMERS; KETONES; STEREOCHEMISTRY; STEREOSELECTIVITY;

ESTERS;

(2R,3R, 6S) 7 (BENZYLOXY) 1 ((TERT BUTYLDIMETHYLSILYL)OXY) 2,6 DIMETHYL 5 METHYLENEHEPTAN 3 OL; (2R,3R,6R) 7 (BENZYLOXY) 1 ((TERT BUTYLDIMETHYLSILYL)OXY) 2,6 DIMETHYL 5 OXOHEPTAN 3 YL 2 (DIETHOXYPHOSPHORYL)ACETATE; (2R,3R,6S) 7 (BENZYLOXY) 1 ((TERT BUTYLDIMETHYLSILYL)OXY) 2,6 DIMETHYL 5 METHYLENEHEPTAN 3 YL 2 (DIETHOXYPHOSPHORYL)ACETATE; (2R,3S,6R) 7 (BENZYLOXY) 1 ((TERT BUTYLDIMETHYLSILYL)OXY) 2,6DIMETHYL 5 OXOHEPTAN 3 YL 2 (DIETHOXYPHOSPHORYL)ACETATE; (2R,3S,6S) 7 (BENZYLOXY) 1 ((TERT BUTYLDIMETHYLSILYL)OXY) 2,6 DIMETHYL 5 METHYLENEHEPTAN 3 OL; (2R,3S,6S) 7 (BENZYLOXY) 1 ((TERT BUTYLDIMETHYLSILYL)OXY) 2,6 DIMETHYL 5 METHYLENEHEPTAN 3 YL 2 (DIETHOXYPHOSPHORYL)ACETATE; (2R,6R,E) 1 (BENZYLOXY) 7 ((TERT BUTYLDIMETHYLSILYL)OXY) 2,6 DIMETHYLHEPT 4 EN 3 ONE; (2S,3R,6R) 7 (BENZYLOXY) 1 ((TERT BUTYLDIMETHYLSILYL)OXY) 2,6 DIMETHYL 5 OXOHEPTAN 3 YL 2 (DIETHOXYPHOSPHORYL)ACETATE; (2S,3R,6S) 7 (BENZYLOXY) 1 ((TERT BUTYLDIMETHYLSILYL)OXY) 2,6 DIMETHYL 5 METHYLENEHEPTAN 3 OL; (2S,3R,6S) 7 (BENZYLOXY) 1 ((TERT BUTYLDIMETHYLSILYL)OXY) 2,6 DIMETHYL 5 METHYLENEHEPTAN 3 YL 2 (DIETHOXYPHOSPHORYL)ACETATE; (2S,3S,6R) 7 (BENZYLOXY) 1 ((TERT BUTYLDIMETHYLSILYL)OXY) 2,6 DIMETHYL 5 OXOHEPTAN 3 YL 2 (DIETHOXYPHOSPHORYL)ACETATE; (2S,3S,6S) 7 (BENZYLOXY) 1 ((TERT BUTYLDIMETHYLSILYL)OXY) 2,6 DIMETHYL 5 METHYLENEHEPTAN 3 OL; (2S,3S,6S) 7 (BENZYLOXY) 1 ((TERT BUTYLDIMETHYLSILYL)OXY) 2,6 DIMETHYL 5 METHYLENEHEPTAN 3 YL 2 (DIETHOXYPHOSPHORYL)ACETATE; (2S,3S,6S) 7 (BENZYLOXY) 1 ((TERT BUTYLDIMETHYLSILYL)OXY) 2,6 DIMETHYL 5 METHYLENEHEPTAN 3 YLACRYLATE; (3R,4S,6S) 4 ((R) 1 (BENZYLOXY)PROPAN 2 YL) 6 ((R) 1 ((TERTBUTYLDIMETHYLSILYL)OXY)PROPAN 2 YL) 3,4 DIHYDROXYTETRAHYDROPYRAN 2 ONE; (3R,4S,6S) 4 ((R) 1 (BENZYLOXY)PROPAN 2 YL) 6 ((S) 1 ((TERTBUTYLDIMETHYLSILYL)OXY)PROPAN 2 YL) 3,4 DIHYDROXY TETRAHYDROPYRAN 2 ONE; (3S,4R,6R) 4 ((R) 1 (BENZYLOXY)PROPAN 2 YL) 6 ((R) 1 ((TERTBUTYLDIMETHYLSILYL)OXY)PROPAN 2 YL) 3,4 DIHYDROXYTETRAHYDROPYRAN 2 ONE; (3S,4R,6R) 4 ((R) 1 (BENZYLOXY)PROPAN 2 YL) 6 ((S) 1 ((TERTBUTYLDIMETHYLSILYL)OXY)PROPAN 2 YL) 3,4 DIHYDROXYTETRAHYDROPYRAN 2 ONE; (R) 4 ((S) 1 (BENZYLOXY)PROPAN 2 YL) 6 ((R) 1 ((TERT BUTYLDIMETHYLSILYL)OXY)PROPAN 2 YL) 5,6 DIHYDROPYRAN 2 ONE; (R) 4 ((S) 1 (BENZYLOXY)PROPAN 2 YL) 6 ((S) 1 ((TERT BUTYLDIMETHYLSILYL)OXY)PROPAN 2 YL) 5,6 DIHYDROPYRAN 2 ONE; (S) (4 (BENZYLOXY) 3 METHYL 2 METHYLENEBUTYL)TRIMETHYLSILANE ((S) 6); (S) 4 ((S) 1 (BENZYLOXY)PROPAN 2 YL) 6 ((R) 1 ((TERT BUTYLDIMETHYLSILYL)OXY)PROPAN 2 YL) 5,6 DIHYDROPYRAN 2 ONE; (S) 4 ((S) 1 (BENZYLOXY)PROPAN 2 YL)6 ((S) 1 ((TERT BUTYLDIMETHYLSILYL)OXY)PROPAN 2 YL) 5,6 DIHYDROPYRAN 2 ONE; DELTA LACTONE; HEMICALIDE; LACTONE DERIVATIVE; POLYKETIDE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; DIHYDROXYLATION; HORNER WADSWORTH EMMONS REACTION; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

LACTONES; MACROLIDES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; POLYKETIDES; STEREOISOMERISM;

EID: 84873380178     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo302440a     Document Type: Article

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