Enantiospecific synthesis of (+)-altholactone and its three stereoisomers

✍ Scribed by Tony K.M. Shing; John G. Gillhouley

• Publisher: Elsevier Science
• Year: 1994
• Tongue: French
• Weight: 937 KB
• Volume: 50
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)85344-8

✦ Synopsis

Altholactone 1 and (+)-7-epi-altholactone 3 were constructed from Dgulonolactone whereas their respective enantiomers (-)-altholactone 2 and (-)J-epialtholactone 4 were synthesised from D-mannose, involving stereocontrolled reduction of the lactols 21 and 12 as a key step.

'I-epi-altholactone 3, and (-)-7-epi-altholactone 4.

Results and Discussion

A. Initial attempt

At the beginning of our research, we arbitrarily chose 2 as our synthetic target only the relative stereochemistry of altholactone was known2 at the time.