Tuesday, May 5, 2009

Swern oxidation typical procedure

Procedure: 25 mL 1-neck flask, stirbar, septum, N2 inlet

Dissolved 0.077 mL of oxalylchloride (II) in 4.0 mL of dry CH2Cl2. Stirred; cooled to -78 C. Added 0.125 mL of DMSO. Stirred 10 min. Added a solution of 0.096 g of alcohol I in 1.0 mL of CH2Cl2. Stirred 15 min. Added 0.250 mL Et3N. After 15 min, warmed to 0 C. After 10 min TLC showed complete reaction. The reaction mixture was placed on a silica gel column and the product was isolated by flash chromatography .

notes

1. temp is critical for high yielding.
2. other than oxalylchloride, many activator can be used to overcome problem caused by oxalylchloride (ex. Cl-), ex. P2O5.


cited from
http://www.alsnotebook.com/oxidswern.html

Monday, May 4, 2009

an approach to Actinophyllic Acid

This synthesis plan was made by me about half a year before Overmann's beautiful synthesis of the same molecular.

An approach to Sordaricin



This proposal is just another application of carbene chemistry in the total synthesis of natural products.