jo5b00972_si_001.pdf (12.43 MB)
Asymmetric Total Synthesis of Bioactive Natural Lipid Mycalol
journal contribution
posted on 2015-06-19, 00:00 authored by Subhendu Das, Tapan Kumar Kuilya, Rajib Kumar GoswamiA concise
and convergent route for stereoselective total synthesis
of promising anticancer natural lipid mycalol has been achieved using
cheap and readily available l-arabinose as a chiral pool.
The notable features of our synthesis comprised regioselective Wacker
oxidation, Sharpless asymmetric dihydroxylation, Julia–Kocienski
olefination, Wittig olefination, Zipper reaction, and Sonogashira
reaction. Comparison of the spectroscopic data on a series of isomers
supports the revised structure (Org. Lett. 2015, 17, 1652) instead of the one originally proposed.