Multi-step reaction with 16 steps
1.1: oxalic acid / acetonitrile / 1.5 h / 20 °C / Inert atmosphere
2.1: tetrahydrofuran / 15 h / 20 °C / Inert atmosphere
3.1: toluene-4-sulfonic acid / acetone / 1.5 h / 20 °C / Inert atmosphere
4.1: sodium tetrahydroborate / dichloromethane; methanol / 0.75 h / 0 °C / Inert atmosphere
5.1: 2,6-dimethylpyridine / dichloromethane / 2.5 h / 20 °C / Inert atmosphere
6.1: boron trifluoride diethyl etherate / dichloromethane / 0.33 h / 0 °C / Inert atmosphere
7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 3.5 h / 20 °C / Inert atmosphere
8.1: tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
9.1: dipyridinium dichromate / dichloromethane / 19 h / 20 °C / Inert atmosphere; Molecular sieve
10.1: toluene-4-sulfonic acid; orthoformic acid triethyl ester / dichloromethane / 64 h / 20 °C / Inert atmosphere
11.1: 2,6-dimethylpyridine / dichloromethane / 1.5 h / 20 °C / Inert atmosphere
12.1: osmium(VIII) oxide; pyridine / diethyl ether / 3 h / 20 °C / Inert atmosphere
12.2: Inert atmosphere
13.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 0.5 h / -78 °C / Inert atmosphere
13.2: -78 - 20 °C / Inert atmosphere
14.1: sodium tetrahydroborate; cerium(III) chloride monohydrate / tetrahydrofuran / 5 h / 0 °C
15.1: dichloromethane / 0.25 h / 20 °C / Inert atmosphere; Molecular sieve
15.2: 0.5 h / -20 °C / Inert atmosphere
16.1: dichloro bis(acetonitrile) palladium(II) / water; acetone / 24 h / 40 - 45 °C / Inert atmosphere
With
pyridine; 2,6-dimethylpyridine; dichloro bis(acetonitrile) palladium(II); sodium tetrahydroborate; osmium(VIII) oxide; dipyridinium dichromate; oxalyl dichloride; cerium(III) chloride monohydrate; boron trifluoride diethyl etherate; oxalic acid; toluene-4-sulfonic acid; dimethyl sulfoxide; orthoformic acid triethyl ester; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; acetone; acetonitrile;
2.1: |Wittig Olefination / 13.1: |Swern Oxidation / 13.2: |Swern Oxidation;
DOI:10.1016/j.tet.2013.06.105