CAS Science Spotlight Most Requested Journal Articles 1Q04-Chemistry and Related


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Most Requested Journal Articles 1Q04-Chemistry and Related

Following is one of the journal articles most requested by researchers using CAS online services.

CAS indexed 34 chemical substances from this document.
CAS subject entries for this document include: Asymmetric synthesis and induction; Cross-coupling reaction; Etherification; and 2 additional concepts.

TITLE:	Enantioselective Total Synthesis of the Potent Antitumor Agent (-)-Mucocin Using a Temporary Silicon-Tethered Ring-Closing Metathesis Cross-Coupling Reaction
AUTHOR(S):	Evans, P. Andrew; Cui, Jian; Gharpure, Santosh J.; Polosukhin, Alexei; Zhang, Hai-Ren
CORPORATE SOURCE:	Department of Chemistry, Indiana University, Bloomington, IN, 47405, USA
SOURCE:	Journal of the American Chemical Society (2003), 125(48), 14702-14703 CODEN: JACSAT; ISSN: 0002-7863
PUBLISHER:	American Chemical Society
LANGUAGE:	English

ABSTRACT:
The enantioselective total synthesis of the annonaceous acetogenin (-)-mucocin (I) was accomplished using a triply convergent 12-step sequence (longest linear sequence) in 13.6% overall yield. This represents the first application of the temporary silicon-tethered (TST) ring-closing metathesis (RCM) cross-coupling reaction and the enantioselective alkyne/aldehyde addn. to the synthesis of a complex annonaceous acetogenin. Moreover, all three fragments required for the coupling reactions are conveniently prepd. in 5-6 steps from two readily available enantiomerically enriched epoxides. Finally, this synthesis stimulated the development of a new approach for the construction of 3-hydroxy-2,6-disubstituted tetrahydropyrans, using the bismuth tribromide-mediated reductive etherification reaction, which represents a motif that is prevalent in a wide range of pharmacol. significant natural products.

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Updated 5/4/2007 7:30:24 AM