Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 9, Issue 1, Pages 367-375Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201301248
Keywords
cyclization; metathesis; natural products; stereoselectivity; total synthesis
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Funding
- JSPS [16GS0206, 16310150]
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The enantioselective total synthesis of the bioactive marine natural products pinnaic acid and halichlorine is reported in detail. Our total synthesis features the construction of the five-membered ring and C9 and C13 stereogenic centers through a palladium-catalyzed trimethylenemethane [3+2] cyclization; the installation of the nitrogen atom through a regioselective Beckmann rearrangement of a poorly reactive ketone; the stereoselective cyclization of the spiro ring through a four-step, one-pot hydrogenation-cyclization; and efficient connection of the sterically hindered lower chain through a reduced-pressure cross olefin metathesis reaction.
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