Aliphatic aldehydes in the synthesis of carbo- and heterocycles: Part II. Synthesis of six- and seven-membered rings, bicyclic compounds, and macrocycles

Abstract

The review summarizes and systematizes data published over the past decade on the use of aliphatic aldehydes in the synthesis of six-and seven-membered carbo-and heterocycles, bicyclic compounds, and macrocycles. Biological activity and synthetic potential of the resulting compounds were also considered. The data are classed according to the ring type formed.

Palladium-Catalyzed β-C–H Arylation of Aliphatic Aldehydes and Ketones Using Amino Amide as a Transient Directing Group

“…Aliphatic aldehydes and ketones are regarded as common structural moieties and the key intermediates in pharmaceuticals, natural products, and chemical synthesis. , In addition, carbonyl compounds also show great value in organic conversion. − However, only a few documents elaborated the C–H functionalization of aldehyde/ketone orientation over transition metal catalysts. − Such methodology is severely hindered by the aldehyde’s weak coordinating capacity, the sensitivity toward oxidation, and the undesired insertion of metal into the acyl C–H bond. To overcome those problems, a method using preinstalled imine or oxime directing group (DG) C–H function was reported.…”

“…14,15 Aliphatic aldehydes and ketones are regarded as common structural moieties and the key intermediates in pharmaceuticals, natural products, and chemical synthesis. 16,17 In addition, carbonyl compounds also show great value in organic conversion. 18−20 However, only a few documents elaborated the C−H functionalization of aldehyde/ketone orientation over transition metal catalysts.…”

Desymmetrization of Hepta-1,6-dien-4-ol by Prins Reaction and Subsequent Cross-Metathesis: Access to Diospongine A Homologues

“…We have considered the design of a common scaffold 4, which could be obtained by desymmetrization of hepta-1,6-dien-4-ol 3 via a Prins reaction promoted by a carboxylic acid like TFA. [10][11][12] To our knowledge, 3 has been implicated only once in a related process during the synthesis of leucascandrolide A. 13 Prins reaction between a secondary homoallylic alcohol and an aldehyde is highly stereoselective leading mainly to the stereomer possessing all substituents in equatorial position.…”