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US 8,912,347 B2Granted
Synthetic transtaganolide and basiliolide products, derivatives thereof, and synthesis methods thereof
AssigneeCalifornia Institute of Technology
InventorsHosea Nelson, Kei Murakami, Scott C. Virgil, Brian M. Stoltz, Jonathan R. Gordon
Life of this patent
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Abstract
Compounds represented by Formula I are provided that include synthetic transtaganolide and basiliolide products. Derivatives of these compounds and methods of synthesis are also provided.
Claims8
A method of synthesizing a compound represented by Formula I, comprising:
- reacting a compound represented by Formula II with a compound represented by Formula III,
- wherein:
- Y is —O(hydrocarbyl);
- M is SnR16R17R18 wherein R16, R17, and R18 are each hydrocarbyl;
- W is —O;
- Wb is —OH or —OSiR30R31R32, wherein R30, R31, and R32 are each hydrocarbyl;
- Z is O;
- R1 is H;
- R2, R3, and R6 are each independently selected from hydrogen and hydrocarbyl;
- R4 is CH3 or CO2CH3;
- R5 is selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, or substituted heteroatom-containing hydrocarbyl;
- and
- R7 and R8 are each independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, or substituted heteroatom-containing hydrocarbyl, wherein two or more adjacent R groups optionally combine to form a ring;
- under conditions sufficient to cause bond formation between a compound of Formula (II) and a compound of Formula (III) to create a coupling adduct;
- and
- contacting the coupling adduct with a proton source to form a compound of Formula (I).
13 more elements
Dependencies are inferred from the claim text.