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Home   •   Spotlight  •  rlist2q06j  •  Most Requested Journal Articles 2Q06-Chemistry and Related (9)

Most Requested Journal Articles 2Q06-Chemistry and Related

Following is one of the journal articles most requested by researchers using CAS electronic products.

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CAS indexed 61 chemical substances from this document. CAS subject entries for this document include: Ring contraction; Crystal structure; Stereoselective synthesis; and 5 additional concepts.

CAPLUS COPYRIGHT 2006 ACS on STN

TITLE:	Concise Total Syntheses of Palominol, Dolabellatrienone, .beta.-Araneosene, and Isoedunol via an Enantioselective Diels-Alder Macrobicyclization
AUTHOR(S):	Snyder, Scott A.; Corey, E. J.
CORPORATE SOURCE:	Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA, 02138, USA
SOURCE:	Journal of the American Chemical Society (2006), 128(3), 740-742 CODEN: JACSAT; ISSN: 0002-7863
PUBLISHER:	American Chemical Society
LANGUAGE:	English

ABSTRACT:
Concise total syntheses of four members, I [R = R' = H (.beta.-araneosene); RR' = O (dolabellatrienone)] , II (palominol) and III (isoedunol), of the dolabellane family of diterpenoid natural products are reported. Key features of the developed route include the first demonstration of an enantioselective, intramol. Type I Diels-Alder macrobicyclization, the first example of a stereoselective .pi.-allyl Stille coupling reaction involving a farnesyl-derived intermediate, a powerful new reagent for the formation of dithianes with acid-sensitive mols., and a unique and highly efficient ring-contraction sequence based on a modified Wolff photochem. rearrangement.