3 years ago

Enantioselective, Protecting-Group-Free Total Synthesis of Boscartin F

Enantioselective, Protecting-Group-Free Total Synthesis
of Boscartin F
Junya Shiraiwa, Kazuyuki Sugita, Akihiko Kasamatsu, Akinobu Matsuzawa
In this work, the protecting-group-free total synthesis and stereochemical assignment of (−)-boscartin F have been reported. The key steps, including Sharpless asymmetric epoxidation, I2-mediated iodoetherification, aldol reaction, and ring-closing metathesis, allowed for rapid and highly stereoselective access to boscartin F. In addition, single-crystal X-ray crystallographic analysis of the semicarbazone derivative 22 confirmed the stereochemistry of boscartin F.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b03979

DOI: 10.1021/acs.orglett.7b03979

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