Total Synthesis of (+)-Pochonin D and (+)-Monocillin II via Chemo- and Regioselective Intramolecular Nitrile Oxide Cycloaddition : Organic Letters 2017

Total Synthesis of (+)-Pochonin D and (+)-Monocillin II via Chemo- and Regioselective Intramolecular Nitrile Oxide Cycloaddition

Asymmetric total syntheses of (+)-pochonin D (1) and (+)-monocillin II (2), Hsp90 inhibitors with potent anticancer activity, have been accomplished where the macrolactone 3 was constructed through a chemo- and regioselective intramolecular nitrile oxide cycloaddition of diene 4.

Total Synthesis of Biselide E, a Marine Polyketide: Organic Letters 2017

Total Synthesis of Biselide E, a Marine Polyketide

The total synthesis of biselide E, a marine polyketide isolated from the Okinawan ascidian, has been accomplished. The highlight of this approach is the use of the β-elimination reaction of the chloroacetoxy group for the construction of an unstable six-membered α,β,γ,δ-unsaturated lactone portion at the late stage of the total synthesis.

Total Synthesis of Paralemnolide A: Organic Letters 2017

Total Synthesis of Paralemnolide A

The first total synthesis of tricyclic bisnorsesquiterpene paralemnolide A, isolated from the soft coral Paralemnalia thyrsoides, was achieved. This synthesis features the lactonization of the cyclohexene derivative having a tert-butyl ester via stereoselective epoxidation followed by treatment with a Brønsted acid and construction of the novel tricyclic skeleton by an intramolecular Reformatsky–Honda reaction.