Studies on Ring-Closing Metathesis for the Formation of the 11-Membered Ring System of Daphnezomine C

For the purpose of synthesizing daphnezomine C, model systems were examined to see if the ring-closing metathesis (RCM) reaction could be applied to prepare an 11-membered ring system bearing a tri-substituted alkene. As a result, it was found that the connectivity pattern of the tethers bearing the...

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Bibliographic Details
Published in:	Bulletin of the Chemical Society of Japan Vol. 80; no. 8; pp. 1597 - 1604
Main Authors:	Tanabe, Kazuhisa, Fujie, Ayako, Ohmori, Naoki, Hiraga, Yoshikazu, Kojima, Satoshi, Ohkata, Katsuo
Format:	Journal Article
Language:	English
Published:	Tokyo The Chemical Society of Japan 15-08-2007 Chemical Society of Japan
Online Access:	Get full text
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Summary:	For the purpose of synthesizing daphnezomine C, model systems were examined to see if the ring-closing metathesis (RCM) reaction could be applied to prepare an 11-membered ring system bearing a tri-substituted alkene. As a result, it was found that the connectivity pattern of the tethers bearing the reacting alkene moieties was crucial. Thus, whereas a system involving a single 1,3- or 1,4-disubstituted cyclohexane derivative did not give RCM products, a flexible system without any rings between the two terminal alkenes gave the cyclic product with a yield of up to 65% using the second generation Grubbs catalyst.
ISSN:	0009-2673 1348-0634
DOI:	10.1246/bcsj.80.1597