A mild procedure for the conversion of 1,2-diols to olefins

✍ Scribed by E.J. Corey; B. Hopkins

• Publisher: Elsevier Science
• Year: 1982
• Tongue: French
• Weight: 238 KB
• Volume: 23
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)87238-x

✦ Synopsis

An improved procedure for the stereospecific synthesis of olefhm from 1,2-dials via the corresponding thionocarbonate is described.

The introduction of the versatile oleflnic function by &oxygenation of a 1,2-diol is a useful technique in organic synthesis. Although numerous procedures have appeared for the conversion of 1,2-dials to the corresponding oleflns, 1 only a few possess the milchess, stereospecificity, and efficiency necessary for their use in multistep synthesis of complex molecules.

In the course of a recent investigation of the chemistry of erythronolide A, 2 the aglycone of the important antibiotic erythromycin A, we attempted the 11,12-deoxygenation of the 3,5-acetonide of erythronolide A (table, entry 7). The most promising of the existing procedures 394 failed with this sensitive substrate and a milder method was required. Herein is reported a modification of the thionocarbonate oleffn synthesis' which was successful in effecting the 11,12-deoxygenation of erythmnolids A-3,5-