CABA + BOCHOMeMeMeOMeOOOHOOOMeMeMeOOMeMeONSOONSO2PhOPhHOOMeOHOOOOHHMeOOMeHOOOMeOOMeOHOOOOHHMe1. P(OPh)3, Br2, TEA
2. t-BuOK, 18-Crown-6, 70°C
3. O3, -78°C
4. Mo(CO)6, Bu4NBr, 90°CAn eight-step gram-scale synthesis
of (−)-jiadifenolide
H. Lu, M. Martinez, R. Shenvi
Nature Chemistry 2015, 7, 604–607.7(−)-jiadifenolide5-65. 1, 120°C
6. SiO27. A, LDA, then B, then Ti(Oi-Pr)4, LDA7. Hint: a double Michael addition1-418. m-CPBA
9. Me4NBH(OAc)3, AcOH
10. LDA, CBr4
11. NaHMDS, 228-11(−)-jiadifenolide1. Name the starting material.
(+)-citronellal
4. Name the reaction.
hetero-Pauson-Khand reaction5. Hint: an acylketene intermediate is generated.11. Name the reagent.
Davis oxaziridine![]()
![]()
![]()
![]()
![]()
![]()
![]()
![]()
![]()
![]()
![]()
![]()
![]()
![]()
![]()