Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 5, Pages 1316-1321Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201711780
Keywords
bielschowskysin; biomimetic synthesis; furanocembranoids; kinetic dearomatization; natural products
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Funding
- BLRD VA [IK2 BX001289, I01 BX004371] Funding Source: Medline
- Veterans Affairs [I01BX004371] Funding Source: NIH RePORTER
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Bielschowskysin (1), the flagship of the furanocembranoid diterpene family, has attracted attention from chemists owing to its intriguing and daunting polycyclic architecture and medicinal potential against lung cancer. The high level of functionalization of 1 poses a considerable challenge to synthesis. Herein, a stereoselective furan dearomatization strategy of furanocembranoids was achieved via the intermediacy of chlorohydrins. The stereochemical course of the kinetic dearomatization was established, and the C3 configuration of the resulting exo-enol ether intermediates proved to be essential to complete the late-stage transannular [2+2] photocycloaddition. Overall, this biomimetic strategy starting from the natural product acerosolide (9) featured an unprecedented regio- and highly stereoselective furan dearomatization, which provided rapid access to the pivotal exo-enol ethers enroute to the intricate bielschowskyane skeleton.
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