A Strategy for the Convergent and Stereoselective Assembly of Polycyclic Molecules

The stereoselective oxidative coupling of cyclic ketones via silyl bis-enol ethers followed by ring-closing metathesis is shown to be a general and powerful reaction sequence for the preparation of diverse polycyclic scaffolds from simple precursors. The modular strategy successfully constructs subs...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 140; no. 5; pp. 1956 - 1965
Main Authors Robinson, Emily E, Thomson, Regan J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.02.2018
Amer Chemical Soc
Subjects
antimalarials
cell lines
Chemistry
Chemistry, Multidisciplinary
cytotoxicity
diterpenoids
ethers
ketones
neoplasm cells
Physical Sciences
Science & Technology
stereoselectivity
CARBON BOND FORMATION
OXIDATION
CATALYSIS
ESTERS
LEADS
INHIBITOR
ENANTIOSELECTIVE TOTAL-SYNTHESIS
1,4-DIKETONES
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ISSN0002-7863
1520-5126
1520-5126
DOI10.1021/jacs.7b13234

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Summary:The stereoselective oxidative coupling of cyclic ketones via silyl bis-enol ethers followed by ring-closing metathesis is shown to be a general and powerful reaction sequence for the preparation of diverse polycyclic scaffolds from simple precursors. The modular strategy successfully constructs substructures prevalent in numerous bioactive natural product families, varying in substitution and carbocyclic composition. Several of the prepared compounds were shown to possess potent cytotoxic activity against a panel of tumor cell lines. The utility of this strategy was further demonstrated by a concise and highly convergent 17-step formal synthesis of the complex antimalarial marine diterpene, (+)-7,20-diisocyanoadociane.
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ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.7b13234