Is anyone able to identify what the name of reaction each is (hydrogenation of a

Question

Is anyone able to identify what the name of reaction each is (hydrogenation of an alkene to an alkane, hydroboration-oxidation, osmylation, protection of an alcohol, Wittig, etc.) in this synthesis of Quinine?

Please!!!

Quinine 01-15 Stork, G., Niu, D., Fujimoto. A; Koft, E. R.; Balkovec, J. M.; Tata, J. R., Dake, G. R. J. Am. Chem. Soc. 2001, 123, 3239 Ph Busio Ph BuSio 1. Et NH/AIMes (AIMe:-NEt 0 1. LIN Prz, -78 C 0 0 0 3. TsOH-Py. Meo [Wittig-methoxymethyl] 1. PPhy, DEAD OSiPh Bu 2. HCI, H.O ?? Ph2Busio 1. DMSO. (COC)," NEt3 (85%) MeO MeO 2. PP, THF, (81%) 0 Mitsunobu Azide] Li-Benzyl+Aldehyde] CompE -Aldehyde/Azide+Li-R] Ketone-?mine! [Staudinger] NaBH4. MeOH Meo Meo Eto2C 1. HF, MeCN 2. MeSO:C, Py IN-HNAlkyl 1. NaH, DMSO O.Et Meo 2. O OH 14:1 Quinine

Explanation / Answer

Step A.

1. Lactone ring opening by diethylamine.

2. protection of hydroxyl group to form the will ether.

Step B

1. Ring closing by tert-butyldiphenylsilyl in a nucleophilic subsitiution by LDA at -780c

2. Removal of the protecting group ( silyl) by TsOH and ring closing by azeotropic distillation.

Step C

1. Reduction by diisobutylaluminium hydride.

2. Wittig reaction to form enol ether.

Step D

1.Mitsunobu reaction by an azide group with diphenylphosphoryl azide.

2.Acid hydrolysis produces azide aldehyde.

Step E

Nucleophilic addition of the lithium salt of 6- methoxy-4-methyl quinoline.

Step F

1. Oxidation of alcohol ( Swern oxidation to ketone)

2. Staudinger reaction with triphenylphosphine closes the ring between ketone and azide.

Step G

Reduction by amine to imine .

Step H

1. Silyl protection group is removed by HF .

2. Activation as mesyl leaving group with mesyl chloride in pyridine which helps to ring closing.

Step I

Hydroxyl group is added by oxidation by Sodium hydride, DMSO and Oxygen.

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