Biomimetic synthesis of trans,syn,trans-fused polyoxepanes: Remarkable substituent effects on the endo-regioselective oxacyclization of polyepoxides

Journal of the American Chemical Society

Volumn 127, Issue 13, 2005, Pages 4586-4587

  Valentine, Jason C ^a   McDonald, Frank E ^a   Neiwert, Wade A ^a   Hardcastle, Kenneth I ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOMIMETIC MATERIAL; EPOXIDE; LEWIS ACID; POLYEPOXIDE DERIVATIVE; POLYOXEPANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOMIMETICS; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CYCLIZATION; METHODOLOGY; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

BIOMIMETIC MATERIALS; CYCLIZATION; EPOXY COMPOUNDS; ETHERS, CYCLIC; SILANES;

EID: 16844371856     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja050013i     Document Type: Article

References (25)

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14. See Supporting Information for experimental details.
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22. Compound 9 also undergoes efficient protiodesilylation (Supporting Information). Careful studies of the protiodesilylation of 9 and 13 reveal that carbonate opening precedes protiodesilylation. The liberated primary alcohol then assists in protiodesilylation via Brook-type silicon migration.
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24. The structure of compound 20 was confirmed by single-crystal X-ray analysis.
25. The structure of compound 23 was confirmed by NOESY spectroscopy.