Synthesis of Decarestrictine D

Structure of Decarestrictine D

C10H16O5

Principal investigator	Ronaldo A. Pilli
Publication year	1998
Synthesis type	Total
Number of steps	15 (3 parts)
References	Tetrahedron Lett. 1997, 39, 4421.

Part 1 of 3

intermediate structure

NaH
TBSCl

THF

0 °C, 91%

intermediate structure

Et3N, DMSO, (COCl)2

CH2Cl2

-78 °C to RT

See the Swern Oxidation

intermediate structure

(EtO)2P(O)CH2CO2Et, NaH

THF

0 °C, 70%

See the Horner-Wadsworth-Emmons Reaction

intermediate structure

AD-mix A, MsNH2

H2O, t-BuOH

94%

See the Sharpless Asymmetric Dihydroxylation

intermediate structure

TBSCl, Imidazole

DMF

100%

intermediate structure

i-Bu2AlH

PhMe

-95 °C

intermediate structure

CHI3, CrCl2

THF

55 °C

See the Takai Reaction

intermediate structure

H2SO4, CrO3

Acetone, H2O

53% (2 steps)

intermediate structure

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Part 2 of 3

intermediate structure

LiAlH4

THF

15 °C to reflux, ON, 85%

intermediate structure

TBSCl

83%

intermediate structure

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Part 3 of 3

intermediate structure

+

intermediate structure

Special reagent

DMAP, Et3N

PhH, THF

83%

See the Yamaguchi Esterification

intermediate structure

Pyr.HF

Pyr, THF

intermediate structure

Dess-Martin Periodinane

CH2Cl2, H2O

See the Dess-Martin Oxidation

intermediate structure

CrCl2, NiCl2

DMF

30% (3 steps)

See the Nozaki-Hiyama-Kishi Reaction

intermediate structure

HF, n-Bu4N+ F-

MeCN

80%

intermediate structure

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