A reliable protocol to synthesize both racemic and chiral (E)-4-iodobut-3-en-1-ols from aldehydes or epoxides, respectively, containing various aromatic and aliphatic substitutions has been established. The utility of these compounds was then demonstrated by providing access to known fungal decanolides as well as novel aromatic macrocycles. The protocol provided a gram-scale route to (-)-aspinolide A and (-)-5-epi-aspinolide A utilizing a catalytic Nozaki-Hiyama-Kishi reaction to close the macrolide in the final step in 65-84% yields.
|Number of pages||13|
|Journal||Journal of Organic Chemistry|
|State||Published - Jan 19 2018|
Bibliographical noteFunding Information:
We acknowledge the following for financial support: DA018151 and GM111385 (to T.E.P.); NIH Training Grant GM08545 (to S.E.W.); The Scientific and Technological Research Council of Turkey (TUBITAK) 1059B141400648 Bezmialem Vakif University (to A.Y.); NSF-MRI Grant CHE-0923449 (to V.W.D.). The support for the NMR instrumentation was provided by the NIH Shared Instrumentation Grant no. S10RR024664 and NSF Major Research Instrumentation Grant no. 0320648.
© 2017 American Chemical Society.
ASJC Scopus subject areas
- Organic Chemistry