Bis ring closing olefin metathesis for the synthesis of unsaturated polycyclic ethers. O-membered ring cyclization in favor of C-membered ring cyclization

Journal of Organic Chemistry

Volumn 64, Issue 9, 1999, Pages 3354-3360

  Baylon, Christophe ^a   Heck, Marie Pierre ^a   Mioskowski, Charles ^b  

^a CEA SACLAY   (France)

^b UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ETHER DERIVATIVE;

CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CYCLIZATION; NOTE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0033617426     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982098u     Document Type: Note

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119. 18
120. 27 yielded eater 18 having complete inversion of configuration. Hydrolysis of 18 followed by alkylation of alcohol 19 afforded 9b. For experimental details and analytical data, see the Experimental Section.
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122. 18
123. 10a was isolated as a mixture of diastereoisomers.
124. The reviewers had very helpful comments concerning the reaction mechanism and the involved intermediates.
125. D was isolated and identified when the RCM reaction was stopped before complete consumption of the starting material. Analytical data are reported in the Experimental Section.