Stereoselective Total Synthesis of Carolacton

A short and convergent strategy for the stereoselective total synthesis of biologically active natural product carolacton has been accomplished. Our synthesis highlights the Urpi acetal aldol, Crimmins aldol, Ireland–Claisen rearrangement, TiCl₄-assisted aldol followed by β-hydroxy elimination to construct C₇–C₈ olefin, and ring-closing metathesis as the key steps for achieving the target molecule with an overall yield of 18.8%

Studies Directed toward the Stereoselective Synthesis of Cytospolide E

Our exhaustive effort toward the total synthesis of cytotoxic marine nonanolide cytospolide E has been detailed. To achieve this synthesis, we have explored both the ring-closing metathesis and lactonization-based macrocyclization strategies using a variety of precursors. Unfortunately, none of them provided the desired product. The ring-closing metathesis approach provided mainly the macrocycle with Z-olefin, whereas the macrolactonization strategy culminated in 8-<i>epi</i>-9-<i>epi</i>-cytospolide E following the regioselective formation of a 10-membered macrocycle over a 9-membered macrocycle

Asymmetric Total Synthesis of Bioactive Natural Lipid Mycalol

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 (<i>Org. Lett.</i> <b>2015</b>, 17, 1652) instead of the one originally proposed