reductive deoxygenation of vinlyl or aryl triflate

Some conditions:

1. pd(PPh3)4/Bu3SnH/THF.
works for vinyl triflate.

2. pd(OAc)2/DPPF/Formic acid/TEA/Bu3SiH/DMF, 50C
works for electron-rich aryl triflate.

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proposal of synthesis of namenamicin

Namenamicin is a enediyne.
the construction of the sulfur-containing quartery center is the critical part of the synthesis. This proposal uses a thionium ion to directly form the quartery center which can lead to the desired structure in an efficient way.

proposal of synthesis of dictyolactone

1.The target is quite an interesting molecular.
2. This proposal mainly aims at the application of C-H insertion in total synthesis.

How to convert indole to tryptamine ?

1. POCl3-DMF to make the indole aldehyde,
2.nitromethane to make unsaturated nitro indole.
3. LAH reduction to give you tryptamine.

to save one step, step 1 and 2 can be made into one step:
TFA, (CH3)2N-CH=CH-NO2, DCM to make the unsaturated nitro indole.

to increase the functional group compatibility of this sequence,
the LAH reduction step can be replaced by a 2 step sequence:
1. NaBH4/SiO2 reduction to take off the double bond.
2. Fe/AcOH reduction to convert the nitro group to amine.