Total synthesis of (-)-spinosyn A: Examination of structural features that govern the stereoselectivity of the key transannular Diels-Alder reaction

Journal of Organic Chemistry

Volumn 73, Issue 5, 2008, Pages 1818-1829

  Winbush, SusAnn M ^a   Mergott, Dustin J ^b,c   Roush, William R ^a  

^a Scripps Florida ^*  (United States)

^b UNIVERSITY OF MICHIGAN   (United States)

^c ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIELS-ALDER REACTION; STEREOCHEMICAL CONTROL;

CONFORMATIONS; CYCLOADDITION; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

10 ETHYL 2,14,BIS(4 METHOXYBENZYLOXY) 15 METHYL 3,3A,10,11,12,13,14,15,18A,18B DECAHYDRO 1H IDENO[5,4 E][1] OXACYCLOPENTADECINE 8,16(2H,5AH)DIONE; 2,14 BIS(4 METHOXY BENZYLOZY) 15 METHYL 3,3A,10,11,12,13,14,15,18A,18B DECAHYDRO 1H INDENO[5,4 E][1]OXACYUCLOPENTADECINE 8,16(2H,5H) DIONE; 2,14 BIS(4 METHOXYBENZYLOXY) 15 METHYL 3,3A,10,11,12,13,14,15,18A,18B DECAHYDRO 1H INDENO[5,4 E][1]OXACCYLOPENTADECINE 8,16 [2H,5AH] DIONE; 20 BROMO 1 (TERT BUTYLDIMETHYSILOXY) 13 ETHYL 9 (4 METHOXYBENZYLOXY) 8 METHYL 2 [(6 DEOXY 2,3,4 TRIMETHYL O METHYL ALPHA MANNOPYRANOSYL)OXY] 2,3,3A,4,18,20A HEXAHYDRO 1H INDENO[5,4 E]OXACYCLOPENTADECA 5,16 DIENE 7,15 DIONE; 20 ETHYL 2,14 BIS(4 METHOXYBENZYLOXY) 15 METHYL 3,3A,10,11,12,13,14,15,18A,18B DECAHYDRO 1H INDENO[5,4 E][1]OXACYCLOPENTADECINE 8,16 (2H,5AH) DIONE; SPINOSYN A; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; BAYLIS HILLMAN REACTION; CHEMICAL STRUCTURE; DIELS ALDER REACTION; STEREOCHEMISTRY; SYNTHESIS;

CYCLIZATION; MACROLIDES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, INFRARED; STEREOISOMERISM;

EID: 41149157530     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo7024515     Document Type: Article

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