AB8–10![]()
1–7![]()
11–15![]()
OOHNH2SOONCNNCNOSiOTBSNOOONBocAcOOCO2MeBrNBrNBrNBrNBrOOSPOSSMeHFFFFFSOHHOHONH3OOHCO2HOOHCO2HNHONHAcPOOOH![]()
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SOHHOHONH3OOHCO2HOOHCO2HNHONHAcPOOOH![]()
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1) 1, amberlyst 15, D
2) 2, Et3N then 2,2,2,trifluoroethanol, TBAF
3) methylene blue, O2, hn then Me2S, SiO2
4) 4-cyanobenzoyl chloride, DMAP
5) CeCl3•7H2O, NaBH4
6) 1,1’-thiocarbonyldiimidazole
7) BHT, 115 °C then PTSA, H2O8) 3, Et3N
9) OsO4, NMO, citric acid then HCl
10) 4, AcOH, D5) Please name the reaction.9) Hint: The most labile protective group
is lost.Total Synthesis of Tagetitoxin
He, C.; Chu, H.; Stratton, T. P.; Kossler, D.; Eberle, K. J.; Flood, D. T.; Baran, P. S.
J. Am. Chem. Soc. 2020, 142, 13683–13688.3) Please provide a mechanism.12311) TfOH, anisole
12) n-Bu3SnH, AIBN then acetone, PTSA
13) MeOH, Et3N then 5, DBN; separation
of diastereomers
14) SeO2
15) TMSOK, H2O then MeONH2•HCl411) Hint: Monodeprotection.5(+)-tagetitoxin(+)-tagetitoxin7) Please classify the reaction.13) Hint: 2 eq of MeOH are consumed.![]()
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