Synthesis of Ziziphine N

Structure of Ziziphine N

C33H49N5O6

Principal investigator	Dawei Ma
Publication year	2007
Synthesis type	Total
Number of steps	17 (3 parts)
References	Org. Lett. 2007, 9, 1367.

Part 1 of 3

intermediate structure

+

intermediate structure

DCC, DMAP

CH2Cl2

0 °C to RT, 3 h

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MeOH

Reflux, 40 min

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NaBH4

CH2Cl2

0 °C, 8 h, 50% (3 steps)

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BH3.Me2S

THF

Reflux, 4 h, 90%

intermediate structure

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Part 2 of 3

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NaOH, CHCl3

EtOH, H2O

70 °C, 3 h, 41%

See the Reimer-Tiemann Formylation

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K2CO3, MeI

DMF

RT, 60 min, 87%

See the Williamson Ether Synthesis

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TMS2NLi, Ph3P+CH2I I-

HMPA, THF

-78 °C to RT, 60 min

See the Wittig Reaction

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Pyr.TsOH

MeOH

RT, 56% (2 steps)

intermediate structure

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Part 3 of 3

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+

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DIAD, Ph3P

THF

80 °C, 3 h, 54%

See the Mitsunobu Reaction

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Me2NCH2CO2H.HCl, Cs2CO3, CuI

Dioxane

80 °C, 12 h, 75%

See the Goldberg Reaction

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n-Bu4N+ F-

THF

RT, 95%

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Dess-Martin Periodinane

CH2Cl2

RT, 2 h

See the Dess-Martin Oxidation

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2-Methyl-2-butene, NaClO2, NaH2PO4

MeCN, t-BuOH

0 °C to RT

See the Pinnick-Lindgren Oxidation

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Me2NH, Pd(PPh3)4

CH2Cl2

RT, 50 min, 56% (3 steps)

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Ph2P(O)OC6F5, i-Pr2NEt

DMF

RT, 24 h, 66%

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ZnBr2

CH2Cl2

0 °C, 4 h

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+

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Special reagent

K2CO3

DMF

0 °C, ON, 22% (2 steps)

intermediate structure

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