Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 129, Issue 15, Pages 4540-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja070571s
Keywords
-
Categories
Funding
- NIGMS NIH HHS [GM 33049] Funding Source: Medline
Ask authors/readers for more resources
A novel diosphenol-based strategy has been developed for the enantioselective synthesis of (-)-terpestacin by multiple usage of the alpha-diketone functionality, first in the Pd AAA-Claisen rearrangement protocol, and second by the employment of its oxidized form, the ene-1,2-dione, as an excellent Michael acceptor. This synthesis demonstrates that the sequence of O-allylation-Claisen rearrangement provides a chemo- and regioselective enolate allylation, which can be performed asymmetrically with respect to the enolate or allyl fragment or both. In addition, many interesting chemoselectivity issues, including a highly selective RCM and a dihydroxylation, have been addressed. Overall, this synthesis was accomplished in 20 longest linear steps (24 total steps) from the inexpensive and commercially available 3-methyl-1,2-cyclopentanedione.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available