The First Stereoselective Total Synthesis of a Naturally Occurring Bioactive Diarylheptanoid, (3R,6E)‐1,7‐Bis(4‐hydroxyphenyl)hept‐6‐en‐3‐ol,through Two Different Approaches

The stereoselective total synthesis of a naturally occurring bioactive diarylheptanoid, (3R,6E)‐1,7‐bis(4‐hydroxyphenyl)hept‐6‐en‐3‐ol, has been accomplished starting from 4‐hydroxybenzaldehyde through two different approaches involving Wittig olefination, hydrolytic kinetic resolution of a racemic epoxide, and olefin cross‐metathesis reaction as the key steps.     

Indium(III) Chloride‐Catalyzed Conversion of {[(Benzyloxy)carbonyl]amino}‐Substituted Sulfones with 2‐[(Trimethylsilyl)oxy]furan: A Facile Access to γ‐Butenolactone Derivatives Containing a Protected Amino Group

Treatment of {[(benzyloxy)carbonyl]amino}‐substituted sulfones 1 with 2‐[(trimethylsilyl)oxy]furan ( 2 ) in the presence of InCl₃ as a catalyst at room temperature produced the γ‐butenolactone derivatives 3 and 4 containing a protected amino group (Scheme 1). The products were formed in high yields (81–92%) within 3–10 h favoring the anti‐isomer 3 .