Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

The stereochemistry of freelingyne and the synthesis of dihydrofreelingyne

CF Ingham and RA Massy-Westropp

Australian Journal of Chemistry 27(7) 1491 - 1503
Published: 1974

Abstract

An unambiguous synthesis of the phenyl analogue of freelingyne from the Wittig reaction of a C5 butenolide phosphorane with (E)-2-methyl-5-phenylpent-2-en-4-yn-l-a1 has confirmed that freelingyne is (2Z,4Z,6E)-9-(3'-furyl)-2,6-dimethylnona-2,4,6-trien-8-yn-4-olide (1). A similar stereo-selective synthesis has shown that the naturally occurring dihydrofreelingyne is (2Z,4Z,6E,8E)- 9-(3'-furyl)-2,6-dimethylnona-2,4,6,8-tetraen-4-olide (2).

https://doi.org/10.1071/CH9741491

© CSIRO 1974

Committee on Publication Ethics


Export Citation Get Permission

View Dimensions