Total stereospecific synthesis of (+) azimic and (+) carpamic acids from D-glucose

✍ Scribed by Stephen Hanessian; Richard Frenette

• Publisher: Elsevier Science
• Year: 1979
• Tongue: French
• Weight: 242 KB
• Volume: 20
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)95417-6

✦ Synopsis

The total synthesis of (+)-azimic and (+)-carpamic acids are described, based on a biomimetic heterocyclization of optically active precursors derived from D-glucose,

The piperidine alkaloids constitute a large family of naturally occurring substances many of which possess important physiological and antibiotic properties'. The macrocyclic dilactones azimine3 and carpaine belong to a small subgroup containing a 2,3,6-trisubstituted piperidine skeleton whose constitutional structures and stereochemistry have been arrived at by spectroscopic and degradative studies. Azimic z and carpamic 2 acids, are stereochemically related and have been shown to be 2(S)-methyl-3(S)-hydroxy-6(R)-(carboxyalkyl)piperidines with an "all cis" configuration, a stereochemical feature found in other piperidinoltype alkaloids as well'. We describe herein a total and stereospecific synthesis of A and 2 from D-glucose, based on the concept of "chiral templates"6, as illustrated in the retrosynthetic analysis shown below.