title: Asymmetric Total Synthesis of Bioactive Natural Lipid Mycalol.
abstract: A 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.
authors.affiliation: Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Kolkata 700032, India.
authors.forename: Subhendu
authors.initials: S
authors.lastname: Das
authors.affiliation: Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Kolkata 700032, India.
authors.forename: Tapan Kumar
authors.initials: TK
authors.lastname: Kuilya
authors.affiliation: Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Kolkata 700032, India.
authors.forename: Rajib Kumar
authors.initials: RK
authors.lastname: Goswami
mesh_terms: D001089:Arabinose / Q000737:chemistry*; D005233:Fatty Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D008055:Lipids / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D005233:Fatty Alcohols; D008055:Lipids; C586897:mycalol; D001089:Arabinose