A Total Synthesis of Linoleic Acid¹

Palladium Catalyzed Synthesis of the Furanoterpene Ircinin-4

“…Due to the inherent lability of the furan rings towards oxidation, the conversion of the resulting alcohol 18 12 to the target must be carried out under carefully controlled conditions and was best achieved by a two step protocol comprising treatment with PDC in CH 2 Cl 2 19 followed by oxidation of the resulting crude aldehyde with AgNO 3 in ethanolic KOH solution. 20 The analytical and spectroscopic data of ircinin-4 (2) thus formed are in full agreement with those reported in the literature. 12,3a…”

Construction of (Z,Z ) skipped 1,4-dienes. Application to the synthesis of polyunsaturated fatty acids and derivatives †

“…One year later, Gensler and Thomas reported a similar approach to the same acid (Scheme 5). 24,25 In 1959, Osbond reported a general route to PUFA, based on the iterative use of propargyl alcohol. Arachidonic 7 (Scheme 6) and docosahexaenoic acids 12 were prepared by this procedure.…”

Glycol Cleavage Reactions

“…Treatment of the dicarbonyl compounds with base causes aldol condensation and hence provides a general method for the preparation of cyclic enones (equation 14)59 or enals (equation 15).60 ( " 0 OTHP (15) Aldol-type cyclization of dialdehydes with nitroalkanes is a valuable synthetic route to amino sugars, amino cyclitols and nucleosides of amino sugars. 65 The glycol cleavage-Wittig condensation sequence has also been employed in the total synthesis of other natural products, e.g. It is noteworthy that the oxidative cleavage of sucrose with LTA affords the dialdehyde selectively (Scheme 8 Generation of aldehydes from oxidative fission of diols for further synthetic elaboration is generally more efficient than that from oxidation of the corresponding primary alcohols.…”