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Paper | Regular issue | Vol 106, No. 4, 2023, pp.649-663
Published online, 22nd March, 2023
DOI: 10.3987/COM-23-14817
■ Stereocontrolled Synthesis of Nitrogen-Substituted Quaternary Stereogenic Centers: Lessons from a Synthetic Route to the Core Structure of Sphingofungin E

Yoshiyasu Ichikawa,* Takahiro Kinutani, Yoshimine Sakogawa, Keisuke Nakanishi, Rika Ochi, Seijiro Hosokawa, and Toshiya Masuda

*Faculty of Science, Kochi University, Akebono-cho, Kochi 780-8520, Japan

Abstract

A strategy has been developed for stereocontrolled synthesis of nitrogen-substituted quaternary stereogenic centers that utilizes enantioselective addition of diethylzinc to α,β-unsaturated aldehydes and allyl cyanate-to-isocyanate rearrangement as key steps. The power and flexibility of this approach was demonstrated by its use in a stereocontrolled synthesis of the core structure of sphingofungin E and its epimer.