mycotrienin I synthesis

Yield:-

Steps:

Multi-step reaction with 19 steps
1.1: 100 percent / BH₃*THF
2.1: 80 percent / CBr₄; PPh₃
3.1: 85 percent
4.1: 100 percent / H₂ / Pd/C
5.1: 70 percent / Me₃Al / benzene
6.1: 98 percent / imidazole
7.1: LHMDS / tetrahydrofuran / -78 °C
7.2: 80 percent / tetrahydrofuran
8.1: 98 percent / Na(Hg); Na₂HPO₄
9.1: 95 percent / HF*Pyr / pyridine
10.1: 80 percent / Pyr*SO₃ / dimethylsulfoxide
11.1: 90 percent / PPTS / acetone
12.1: 70 percent / CrCl₂
13.1: Pd(MeCN)2Cl₂ / dimethylformamide; tetrahydrofuran
14.1: pTsOH / methanol
15.1: DMAP / CH₂Cl₂ / -78 °C
16.1: Et₂NH / CH₂Cl₂
17.1: BOP; Et₃N / CH₂Cl₂
18.1: CAN / tetrahydrofuran; H₂O
19.1: aq. HF / acetonitrile

References:

Panek, James S.;Masse, Craig E. [Journal of Organic Chemistry,1997,vol. 62,# 24,p. 8290 - 8291]