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

Autor:	Yoshitaka Araki, Toshiro Konoike
Rok vydání:	1998
Předmět:	Enyne Methanesulfonyl chloride Silylation Organic Chemistry Cumulene Alcohol Conjugated system Biochemistry Medicinal chemistry chemistry.chemical_compound chemistry Drug Discovery Neocarzinostatin chromophore Triethylamine
Zdroj:	Tetrahedron Letters. 39:5549-5552
ISSN:	0040-4039
DOI:	10.1016/s0040-4039(98)01117-4
Popis:	Sequential treatment of a propargylic alcohol by BuLi and Bu 3 SnCl 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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::da0c8131d19fd5c3ac168489c1576979 https://doi.org/10.1016/s0040-4039(98)01117-4 Zobrazit plný text záznamu Full Text from ScienceDirect