Multi-step reaction with 15 steps
1.1: 33 percent / I2; PhI(OAc)2 / CH2Cl2 / 0 °C / Photolysis
2.1: 85 percent / i-Pr2NEt / CH2Cl2 / 20 °C
3.1: O3 / CH2Cl2 / -78 °C
3.2: 89 percent / Ph3P / CH2Cl2 / -78 - 20 °C
4.1: Zn(BH4)2 / diethyl ether / 0 °C
5.1: tetrabutylammonium fluoride / tetrahydrofuran / 0 °C
6.1: 93 percent / PPTS / acetone / 20 °C
7.1: 86 percent / LHMDS; HMPA / tetrahydrofuran / -78 °C
8.1: O3 / CH2Cl2 / -78 °C
8.2: Ph3P / CH2Cl2 / -78 - 20 °C
9.1: NaBH4 / methanol / 20 °C
10.1: o-O2NC6H4SeCN; Bu3P / tetrahydrofuran / -78 - 20 °C
11.1: LiAlH4 / dioxane / Heating
12.1: 90 percent / Et3N / CH2Cl2 / 20 °C
13.1: 94 percent / TPAP; 4-methylmorpholine N-oxide / acetonitrile / 20 °C
14.1: O3 / CH2Cl2 / -78 °C
14.2: Ph3P / CH2Cl2 / -78 - 20 °C
15.1: SmI2; HMPA / tetrahydrofuran / -40 °C
With
N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; lithium aluminium tetrahydride; ortho-nitrophenyl selenocyanate; samarium diiodide; tetrapropylammonium perruthennate; zinc(II) tetrahydroborate; tributylphosphine; [bis(acetoxy)iodo]benzene; tetrabutyl ammonium fluoride; iodine; pyridinium p-toluenesulfonate; ozone; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane;
In
tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; acetone; acetonitrile;
1.1: Dehydrogenation / 2.1: Alkylation / 3.1: ozonation / 3.2: Ring cleavage / 4.1: Reduction / 5.1: Elimination / 6.1: Cyclization / 7.1: Acylation / 8.1: ozonation / 8.2: Ring cleavage / 9.1: Reduction / 10.1: Dehydration / 11.1: Reduction / 12.1: Substitution / 13.1: Oxidation / 14.1: ozonolysis / 14.2: Ring cleavage / 15.1: Cyclization;
DOI:10.1021/ol000290o