Skip to main content
. Author manuscript; available in PMC: 2020 Jun 21.
Published in final edited form as: Org Lett. 2019 Jun 11;21(12):4873–4877. doi: 10.1021/acs.orglett.9b01770

Scheme 1. Synthesis of (±)-Hyalodendrin 2a.

Scheme 1.

a Conditions: (a) LiHMDS, THF, −78 °C, S-[[(tert-butyldimethylsilyl)oxy]methyl] 4-methylbenzenesulfonothioate, 85%; (b) LiHMDS, THF, DMPU, 0 °C, BnBr, 84%; (c) TBAF, TrSCl, THF, 85%; (d) MeMgBr, THF, −78 °C; (e) PTSA, DCM, 58% (over two steps); (f) OsO4, NMO, acetone/H2O, 89%; (g) BF3·OEt2, DCM, −78 °C to rt, 70%.