aciculatin synthesis

Yield:-

Steps:

Multi-step reaction with 6 steps
1: N-iodo-succinimide; trifluorormethanesulfonic acid / dichloromethane; diethyl ether / 18 h / -40 - 20 °C / Molecular sieve
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / N,N-dimethyl-formamide / 16 h / 60 °C
3: sodium hydride / tetrahydrofuran / 1.17 h / 0 - 80 °C
4: camphorsulfonic acid / toluene / 6 h / 130 °C / Inert atmosphere
5: boron tribromide / dichloromethane / 5 h / -78 - 0 °C / Inert atmosphere
6: sodium methylate / methanol; dichloromethane / 18 h / -20 - 0 °C

References:

Yao, Chun-Hsu;Tsai, Chi-Hui;Lee, Jinq-Chyi [Journal of Natural Products,2016,vol. 79,# 7,p. 1719 - 1723]