Total Syntheses

Reaction scheme for total synthesis of the natural product Clausenane <b><i><font color=green>New</font></i></b>
Total synthesis of Clausenane New:
Reference:Kondo, K.; Matsumoto, M. Tetrahedron Lett. 1976, 17, 4363-4366. DOI
Reactions:Mg-Vinyl+Aldehyde • Singlet oxygen+Diene • Furan synthesis • Iodoetherification • Ether-5 • Li-Dithiane+Alkyl-X • Alkyl-X+Li-R • Li-Dithiane+Alkyl-X • Alkyl-X+Li-R • Ketal(thio) → Ketone • Dehydration → Ene • Li/H → Li-Dithiane •
Reagents:Butadiene • O2 (singlet) • Rose Bengal • LiOtBu • H2SO4 • NIS • Bicarbonate, sodium • HMPA (solvent) • BuLi(n) • HMPA (solvent) • AgNO3 • NCS • Bisulfate, potassium •