Six-Step Total Synthesis of Azaspirene

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The total synthesis of (+/-)-azaspirene (1) was achieved in a total of six steps from commercially available materials. Keys to the conciseness of our synthetic approach were the effective gamma-lactam formation from linear precursor 36 and successful tandem epoxidations of gamma-lactam 34 to afford alpha,beta-epoxy-gamma-hydroxy-gamma-lactam intermediate 14. While our streamlined synthesis of azaspirene (1) sought inspiration from its biogenetic hypothesis, experimentally observed chemical reactivity of biosynthetically relevant precursors conversely provides insights to the biological origin of this natural product.
Publisher
AMER CHEMICAL SOC
Issue Date
2017-07
Language
English
Article Type
Article
Keywords

ASYMMETRIC TOTAL-SYNTHESIS; ANGIOGENESIS INHIBITOR; (+/-)-BERKELEYAMIDE D; PSEUROTIN-A; (-)-AZASPIRENE; BIOSYNTHESIS; METABOLITE; PRODUCT

Citation

JOURNAL OF ORGANIC CHEMISTRY, v.82, no.18, pp.9335 - 9341

ISSN
0022-3263
DOI
10.1021/acs.joc.7b01224
URI
http://hdl.handle.net/10203/226645
Appears in Collection
CH-Journal Papers(저널논문)
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