AB5-7![]()
1-4![]()
OCHOBrOOOMOMOOOOMeOOOOMeOOMeOOMeOMeOOBzOOHMeOMeOOMeOOOOMeOOMeOOMeOMeOOBzOOHMeOMeOOMeOOMeOTBSSiOTIPSOMeOOOMOMOOOBMeOHMeOOOMOMOOOHOOMeOOMeOSiOTIPSMeOOMeBMeOBO(R)OHHSiTIPSCyCyMeH96![]()
![]()
SiOTIPSOOMeOH69![]()
![]()
OOMeOOMeSiOTBSOSiOTIPSOOMe6![]()
OCHOBrOOOMOMOO![]()
thenSiOTIPSOOMeOH69![]()
![]()
SiOTIPSOMeOHMeOH7![]()
![]()
TiOOMeClClClOSiOTIPSHCH3Me![]()
7![]()
![]()
OTBSOMeOMeOMeOTIPSTSTSMimicking oxidative radical cyclization of lignan biosynthesis using redox-neutral photocatalysis
Zheng, H; Lumb, J. P.
Nat. Chem. 2021, 13, 24-32.1) TMPMgBr, Cy2BCl, then 1
2) TiCl4, LiH, MeMgCl
3) MeB(OH)2
4) t-BuLi5) KHF2
6) DBDMH
7) SPhos Pd G2/ SPhos (cat.), K3PO41) Explain the Stereoselectivity of Step 1; draw the transition state
2) Draw the transition state for step 2.
See Page 37) Please name the reaction for step 7
Suzuki Coupling (Buchward’s Condition)
citation: JACS, 2010, 132, 14073.18-14Heteroclitalignan Dsolution to step 1:8) MeI, then H2O2
9) BzCl, DMAP
10) TBAF
11) IBX, then NaBH4
12) Ac2O, DMAP
13) NaHSO4 SiO2
14) MeI, Cs2CO3Heteroclitalignan DTMPMgBr,
Cy2BCl9TiCl4, LiH
MeMgClsolution to step 2:![]()
![]()
![]()
![]()
![]()
![]()
![]()
![]()
![]()
![]()
![]()
![]()
![]()
![]()
![]()
![]()
![]()
![]()
![]()
![]()