A new route to cumulenes by stannylation-deoxystannylation of propargylic alcohols. Application to synthesis of conjugated enyne[3]cumulene as a model compound of neocarzinostatin chromophore

✍ Scribed by Yoshitaka Araki; Toshiro Konoike

• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 273 KB
• Volume: 39
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(98)01117-4

✦ Synopsis

Sequential treatment of a propargylic alcohol by BuLl and Bu3SnCI gave a mixture of stannylated propargylic alcohol and stannylated allenyl alcohol, both of which were converted to a single [3]cumulene by deoxystannylation of the stannyl alcohols by treatment with methanesulfonyl chloride and triethylamine. The efficiency of the deoxystannylation has been compared with that of an analogous silyl counterpart and proved to be much more efficient. The method has been applied to synthesis of conjugated enyne[3]cumulene 3 as a model compound of neocarzinostatin chromophore.