Barium manganate alcohols with

The oxidation of diols having alcoholic groups of the same nature, for example, both alcoholic groups are primary, secondary, allylic, or benzylic, is usually carried out at both groups to yield dialdehydes [832] or diketones [552], Such reactions are achieved by chromium trioxide [582], barium manganate [832], dimethyl sulfoxide activated with acetic anhydride [1013], and others (equations 284 and 285). 

A second total synthesis of ascididemin (323) was achieved by Moody et al. in 1990 in two steps starting from l,10-phenanthroline-5,6-quinone (331) (Scheme 38) (155,156). The quinoneimine 333 was first prepared by reaction between the quinone 331 and the sodium salt of diethyl N-(2-iodophenyl)-phosphoramidate (332). Photocyclization of 333 in cone, sulfuric acid gave ascididemin (323). Because of the low yield of especially the first step, 10%, preparation of 333 was carried out via a different route in two steps. The reaction of epoxide 334 with 2-iodoaniline 335 gave the amino alcohol 336, which was readily oxidized with barium manganate to the desired intermediate 333. 

The readily available and stable compound barium manganate has been shown to be an efficient oxidizing agent for the oxidation of primary and secondary alcohols to carbonyl compounds. It has similar activity to manganese dioxide but is claimed to be better for the preparation of certain aldehydes e.g. the furan aldehyde (11) is produced in 80% yield whereas with Mn02 the yield is less than 20%. 

---