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Catalytic Asymmetric Synthesis of Hexahydro-furofuran-3-ol and Its Pyran Derivatives. | LitMetric

Catalytic Asymmetric Synthesis of Hexahydro-furofuran-3-ol and Its Pyran Derivatives.

Org Lett

Department of Chemistry, Pohang University of Science and Technology (POSTECH), 77 Cheongam-Ro, Nam-gu, Pohang, Gyeongbuk, Republic of Korea 37673.

Published: May 2021

The catalytic asymmetric synthesis of hexahydro-furofuran-3-ol, a key fragment of HIV protease inhibitors, is reported. A signature event is represented by the sequential metal catalysis that combines the Pd-catalyzed asymmetric hydroalkoxylation of ene-alkoxyallene and ring-closing metathesis (RCM). Notably, this unprecedented and highly chemoselective approach allows for a unified access to pyranofuranol and furopyranol derivatives.

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http://dx.doi.org/10.1021/acs.orglett.1c00981DOI Listing

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