Question: Can someone work out this synthesis Steps/Reagents 1. CH 3 CH 2 OH,H + 2. dihydropyran,H + 3. LiAlH 4 ,then H 2 O 4.

Can someone work out this synthesis

HOOC COOH (R)-Malic acid (1) A (C8H1405) (2) D B (5) (3)

Steps/Reagents

1. CH 3 CH 2 OH,H +

2. dihydropyran,H +

3. LiAlH 4 ,then H 2 O

4. TsCl, pyridine

5. Nabr, DMSO

6. H 2 O, CH 3 COOH

7. KOH

This stereospecific synthesis, starting with enantiometrically pure (R)-malic acid, yields a bromoepoxide,

HOOC COOH (R)-Malic acid (1) A (C8H1405) (2) D B (5) (3) E C (C9H1804) (6) (4) F (C4H8OBr) (7) A bromoepoxide

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