Synthesis of pseudopterane analogues by intramolecular S(E)2' cyclization

Journal of Organic Chemistry

Volumn 64, Issue 14, 1999, Pages 5193-5200

  Marshall, James A ^a   McNulty, LuAnne M ^a   Zou, Dong ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFLAMMATORY AGENT; CYTOTOXIC AGENT; NATURAL PRODUCT; PSEUDOPTERANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; ESTERIFICATION; NONHUMAN; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0033067673     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990376z     Document Type: Article

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17. 12 MM2 force field) showed relative energies of 283 and 311 kJ/mol for the Z and E syn isomers of the methyl ester analogue of 15.
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25. 16 Thus, it can be surmised that equilibration of these reagents is relatively fast. On the other hand, crotyltin trichloride has been shown to undergo a rather slow E/Z isomerization affording a 2:1 mixture favoring the E isomer. Nartuta, Y.; Nishigaichi, Y.; Maruyama, K. Tetrahedron 1989, 45, 1067.
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