Advices For Studying Organic Chemistry

5. The tartrate (either diethyl or diisopropyl ester) stereoisomer that is chosen
   depends on the specific enantiomer of the epoxide desired.

1. It is possible to prepare either enantiomer of a chiral epoxide in high
   enantiomeric excess:

OH

(+)-dialkyl tartrate

(−)-dialkyl tartrate

OH

OH

O

O

(S)-Methylglycidol

(R)-Methylglycidol

Sharpless asymmetric epoxidation

Sharpless asymmetric epoxidation

6. The synthetic utility of chiral epoxy alcohol synthons produced by the Sharpless
   asymmetric epoxidation has been demonstrated in enantioselective syntheses of
   many important compounds.

1. Polyether antibiotic X-206 by E. J. Corey (Harvard University):

H OOH O

OH

O

O

O

HHOH

OH

H OH HO H
OOH

Antibiotic X-206

2) Commercial synthesis of the gypsy moth pheromone (7R,8S)-disparlure by J. T.

Baker:

O

H

H

(7R,8S)-Disparlure