Synthesis of Phyllantidine

C13H15NO3

Part 1 of 1

Yb(OTf)3

4Å MS

PhMe

RT to Reflux, ON, 86%

LiCl

DMSO, H2O

160 °C, 2 h, 85%

See the Krapcho Decarboxylation

TMS2NK

THF

-78 °C, 2.5 h, 80 &

LiAlH4

THF

0 °C, 2 h, 97%

"The major diastereoisomer was separated via its acetonide in (52 % yield)."

IBX

DMSO

RT, 2 h, 64%

VinylMgBr

THF

0 °C, 3 h, 76%

See the Grignard Reaction

IBX

DMSO

RT, 2 h, 79%

Grubbs catalyst (2nd gen.)

CH2Cl2

Reflux, 2 h, 74%

See the Olefin Metathesis

DCC

CH2Cl2

RT, 60 min, 71%

18-Crown-6, K2CO3

PhMe

RT, 2.5 h, 100%

DDQ

CH2Cl2, H2O

RT, ON, 98%

DIAD, Ph3P

PhH

RT, ON, 98%

See the Mitsunobu Reaction