Synthesis of the schweinfurthin hexahydroxanthene core through Shi epoxidation

Use of a Shi epoxidation for introduction of chirality in a key epoxide intermediate, together with revised protecting group tactics, has allowed an efficient synthesis of the hexahydroxanthene subunit common to the natural schweinfurthin F and the synthetic analogue 3-deoxyschweinfurthin B.

Graphical abstractUse of a Shi epoxidation for introduction of chirality in a key epoxide intermediate, together with revised protecting group tactics, has allowed an efficient synthesis of the hexahydroxanthene subunit common to the natural schweinfurthin F and the synthetic analogue 3-deoxyschweinfurthin B.Download full-size image