Total synthesis of Davanone:
| Reference: | Morrison, K. C.; Litz, J. P.; Scherpelz, K. P.; Dossa, P. D.; Vosburg, D. A. Org. Let. 2009, 11, 2217. DOI |
| Reactions: | CarboxEster → CarboxAmide(Weinreb) • CarboxAmide(Weinreb)+Mg-R • Mg-Alkyl+CarboxAmide • Allylic oxidation → Allyl-OH • CompOx-Alkene/Alkene+SeO2 • Sharpless epoxidation • Bode epoxide elimination • Pd-allyl-O coupling • Ether-5 • Tsuji-Trost allylation • Ether-5 • Alkyl-OH → Aldehyde • |
| Reagents: | SeO2 • Epoxide • Hydroperoxide, tbutyl • DMSO, Py·SO3 (Parikh-Doering) • Thiazolium • Pd2(dba)3 • Chiral catalyst (phosphine) • TunePhos • Allyl-MgX • NHMe(OMe) • Alkyl-MgX • Hydroperoxide, tbutyl - Ti • HOEt (react)} • |