期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 131, 期 6, 页码 2348-2358出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja8084669
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资金
- National Institutes of Health
- National Cancer Institute [CA-19033, CA-101532]
An effective, asymmetric total synthesis of the antitumor antibiotic (-)-okilactomycin (1), as well as assignment of the absolute configuration, has been achieved exploiting a convergent strategy. Highlights of the synthesis include a diastereoselective oxy-Cope rearrangement/oxidation sequence to install the C(1) and C(13) stereogenic centers, a Petasis-Ferrier union/rearrangement to construct the highly functionalized tetrahydropyranone inscribed within the 13-membered macrocycle ring, employing for the first time a sterically demanding acetal, an intramolecular chemoselective acylation to access an embedded bicyclic lactone, and an efficient ring-closing metathesis (RCM) reaction to generate the macrocyclic ring.
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