A concise synthesis of (2 S,3 S,4 S)-2-(hydroxymethyl)pyrrolidine-3,4-diol (LAB1)

Article abstract of DOI:10.1055/s-0030-1258185

The synthesis of (2S,3S,4S)-2-(hydroxymethyl)pyrrolidine-3,4-diol (LAB1) from Garners aldehyde is described using the Sharpless asymmetric dihydroxylation as the key step. Georg Thieme Verlag Stuttgart - New York.

Full text of DOI:10.1055/s-0030-1258185

FEATURE ARTICLE
3063
A Concise Synthesis of (2S,3S,4S)-2-(Hydroxymethyl)pyrrolidine-3,4-diol
(LAB1)
(
2
S
,3
S
,4
S
)-2-(
u
H
ydroxyme
t
s
hyl)pyrrol
p
idine-3, 4-dio
e
l
(LAB1) sh K. Upadhyay, Pradeep Kumar*
Division of Organic Chemistry, National Chemical Laboratory, Pune 411 008, India
Fax +91(2)25902629; E-mail: pk.tripathi@ncl.res.in
Received 25 May 2010; revised 15 June 2010
of its synthesis from Garner’s aldehyde. As part of our re-
search on the enantioselective synthesis of naturally oc-
curring amino alcohols,12 we aimed to synthesize an
intermediate such as LAB1 from an a-amino aldehyde,
which could be useful in the synthesis of variety of com-
pounds, such as 2–5, of biological interest (Figure 1).
Abstract: The synthesis of (2S,3S,4S)-2-(hydroxymethyl)pyrroli-
dine-3,4-diol (LAB1) from Garner’s aldehyde is described using the
Sharpless asymmetric dihydroxylation as the key step.
Key words: Garner’s aldehyde, Wittig reaction, diastereoselectivi-
ty, alkaloid, azasugars, pyrrolidine
OH
OH
OH
HO
HO
HO
Hydroxylated pyrrolidines constitute one of the main
classes of naturally occurring sugar mimics having nitro-
gen in the ring.1 Among them, 1,4-dideoxy-1,4-imino-D-
arabinose and -D-ribose are naturally occurring imino sug-
ars exhibiting activity as glycosidase inhibitors.2 Much at-
tention has been focused on this class of compounds
because of their potential for therapeutic applications and
also their role as glycosidase inhibitors.3
HO
N
N
H
N
H
H
1
2
3
2-methyl-3,4-dihydroxy-
pyrrolidine
2-ethyl-3,4-dihydroxy-
pyrrolidine
LAB1
OH
OH
HO
HO
a-Amino aldehydes are versatile building blocks that are
frequently used in the synthesis of natural products.4 Ad-
ducts of a-amino aldehydes and acetylenic compounds are
easily transformed into a variety of chiral natural products
containing many contiguous stereogenic centers. Among
these products are glycosidic antibiotics,5 cytostatic,6 an-
tihelmintic,7 as well as antiviral compounds.8
HO
N
N
4
5
swainsonine
lentiginosine
Figure 1 Structures of polyhydroxylated pyrrolidine and indolizi-
dine alkaloids
Various synthetic methods for the synthesis of hydroxy-
substituted pyrrolidines have been reported either from
carbohydrates,9 as a chiral pool starting material, or from
other sources.10 The syntheses of target molecule LAB1 A synthetic approach for the synthesis of (2S,3S,4S)-2-
(1) described in the literature use either carbohydrate,11a,b (hydroxymethyl)pyrrolidine-3,4-diol (1,4-dideoxy-1,4-
enzyme,11c amino acid,11d tartaric acid,11e or miscella- imino-L-arabinitol, LAB1, 1) was envisioned via the syn-
neous approaches.11f Surprisingly there has been no report thetic route shown in Scheme 1.
OH
O
O
OH
HO
OEt
OMs
HO
O
O
N
OH
N
N
H
O
Boc
Boc
1
6
7
O
CHO
CO2H
NH2
HO
O
OEt
O
N
N
Boc
Boc
8
9
10
L-serine
Garner's aldehyde
Scheme 1 Retrosynthetic analysis of LAB1 (1)
SYNTHESIS 2010, No. 18, pp 3063–3066
x
x.
x
x
.
2
0
1
0
Advanced online publication: 16.07.2010
DOI: 10.1055/s-0030-1258185; Art ID: Z13110SS
© Georg Thieme Verlag Stuttgart · New York

3064
P. K. Upadhyay, P. Kumar
FEATURE ARTICLE
OH
O
O
CHO
CO2H
a
b
c
OEt
O
O
OEt
HO
O
N
OH
N
N
NH2
Boc
Boc
Boc
OH
10
9
8
7
L-serine
O
O
O
O
OH
HO
e
d
f
g
OMs
OEt
HO
O
O
O
N
O
N
N
N
O
O
H
Boc
Boc
Boc
11
12
6
1
LAB1
Scheme 2 Synthesis of LAB1 (1). Reagents and conditions: (a) (i) Boc2O, 1 M NaOH, dioxane, H2O, 0 °C to r.t., 3.5 h; (ii) MeI, K2CO3,
DMF, 0 °C to r.t., 2 h, 86%; (iii) 2,2-DMP, acetone, BF3·OEt2, 2 h, 90%; (iv) DIBAL-H, –78 °C, anhyd toluene, 1–2 h, 75%; (b)
Ph3P=CHCO2Et, anhyd THF, 60 °C, 5 h, 90%; (c) OsO4, (DHQ)2PHAL, K3Fe(CN)6, K2CO3, MsNH2, t-BuOH–H2O, 0 °C, 24 h, 92%; (d) 2,2-
DMP, TsOH, anhyd toluene, reflux, 30 min, 96%; (e) LiAlH4, anhyd THF, 0 °C to r.t., 1 h, 75%; (f) MsCl, Et3N, DMAP, anhyd CH2Cl2, 0 °C,
2 h, 81%; (g) 2 M HCl, EtOAc, 0 °C, 3 h, then sat. NaHCO3 soln (to pH 8), 1 h, 69%.
As depicted in Scheme 1, the target molecule LAB1 (1) Garner’s aldehyde 9 was prepared from L-serine in 58%
could be obtained from mesylate 6, which in turn could be overall yield.13 The freshly prepared Garner’s aldehyde 9
accessed from a,b-diol ester 7. Compound 7 would be was subjected to two-carbon homologation by Wittig re-
prepared by dihydroxylation of olefin 8, which in turn action to give the olefinic ester 8 in 90% yield. We carried
could be synthesized from Garner’s aldehyde 9 derived out dihydroxylation reaction under Sharpless asymmetric
from L-serine (10).
conditions14 using (DHQ)2PHAL ligand and osmium
tetroxide to produce dihydroxy ester 7 in 92% yield.15
Acetonide protection of compound 7 with 2,2-dimethoxy-
propane (2,2-DMP) in the presence of a catalytic amount
The synthesis of target molecule LAB1 (1) began from
commercially available chiral pool starting material L-
serine (Scheme 2). Following the literature procedure,
Biographical Sketches
Puspesh
Kumar
Up- the group of Dr. Pradeep from Pune University, Pune,
adhyay was born in India in Kumar at the National India in 2010 under the su-
1976. He obtained his B.Sc. Chemical Laboratory, Pune, pervision of Dr. Pradeep
and M.Sc. degrees from India, from 2001–2004. Kumar. At present (since
Purvanchal
University, Subsequently he joined the February 2010) he is work-
Jaunpur (UP), India. After same group as a senior re- ing in the Laxai Pharma
that, he gained research ex- search scholar for his doc- Company, Hyderabad in the
perience as a project assis- toral thesis in 2005. He Discovery Division as an
tant in various projects in obtained his Ph.D. degree Associate Scientist.
Pradeep Kumar was born Bestmann at the Institute of Germany (2006 and 2010).
and grew up in India. He re- Organic Chemistry, Univer- He has published over 140
ceived his B.Sc. and M.Sc sity of Erlangen, Nurem- papers and a few review ar-
degrees from Gorakhpur berg during 1988–1990 as a ticles in international jour-
University. In 1981, he ob- DAAD fellow and later as nals of repute. He is a fellow
tained his Ph.D. degree un- an Alexander von Humboldt of the National Academy of
der the supervision of the fellow
with
Professor Sciences of India. He is re-
late Professor Arya K. Muk- Richard R. Schmidt at the cipient of the bronze medal
erjee. Subsequently he University of Konstanz, (2009–2010) of chemical
joined the National Chemi- Germany
(1996–1997), research society of India.
cal Laboratory, Pune, India with Professor Martin E. His research interest in-
in 1982. He has been work- Maier at the University of cludes the development of
ing in the Organic Chemis- Tuebingen,
Germany new methodologies, synthe-
try Division as Scientist G (2003), with Professor J. sis of biologically active
since 2008. He visited Rademann at Leibniz Insti- natural products, and solid
Germany and worked in the tute for Molecular Pharma- catalyst induced synthetic
group of Professor H. J. cology (FMP), Berlin, organic transformation.
Synthesis 2010, No. 18, 3063–3066 © Thieme Stuttgart · New York

FEATURE ARTICLE
(2S,3S,4S)-2-(Hydroxymethyl)pyrrolidine-3,4-diol LAB1
3065
with EtOAc (3 × 50 mL). The combined organic extracts were
washed with 10% KOH soln and brine, dried (Na2SO4), and concen-
trated. The crude product was subjected to column chromatography
(silica gel, PE–EtOAc, 80:20) to give 7 as a colorless syrupy liquid;
yield: 2.15 g (92%).
[a]D25 –22.03 (c 0.82, CHCl3) [Lit.15 [a]D20 –21.2 (c 0.82, CHCl3)].
IR (CHCl3): 3435, 1719 cm–1.
1H NMR (200 MHz, CDCl3): d = 1.29 (t, J = 7.20 Hz, 3 H), 1.48–
1.56 (m, 15 H), 3.86–3.94 (m, 2 H), 3.99–4.05 (m, 1 H), 4.14–4.20
(m, 2 H), 4.23 (q, J = 7.2 Hz, 2 H), 4.73 (br s, 1 H).
13C NMR (50 MHz, CDCl3): d = 13.9, 23.8, 28.1, 58.6, 61.3, 65.2,
70.4, 72.8, 81.7, 94.0, 154.3, 171.4.
of 4-toluenesulfonic acid furnished 11 in essentially quan-
titative yield. The ester moiety of compound 11 was re-
duced with lithium aluminum hydride to give the amino
alcohol 12 in 75% yield, which on treatment with meth-
anesulfonyl chloride using a catalytic amount of 4-(di-
methylamino)pyridine gave the mesylated compound 6 in
81% yield.
Finally, global deprotection of 6 with 2 M hydrochloric
acid followed by subsequent cyclization gave the target
molecule 1 in 69% yield. The spectral properties (1H and
13C NMR) of 1 were in full agreement with those reported
in the literature.11f
MS (ESI): m/z = 334 (M+ + 1), 356 (M+ + Na), 372.3 (M+ + K).
In summary, we have achieved a short synthesis of
(2S,3S,4S)-2-(hydroxymethyl)pyrrolidine-3,4-diol (LAB1)
in seven steps in 19% overall yield starting from L-serine
and using the Sharpless asymmetric dihydroxylation as
the key step.
Ethyl (2R,3S)-3-[(S)-3-(tert-Butoxycarbonyl)-2,2-dimethylox-
azolidin-4-yl]-2,3-(isopropylidenedioxy)propanoate (11)
To a soln of the diol 7 (0.5 g, 1.51 mmol) in anhyd toluene (16 mL)
was added 2,2-dimethoxypropane (5 mL) and TsOH·H2O (6.3 mg,
0.03 mmol). The mixture was refluxed for 30 min and then treated
with sat. aq NaHCO3 (10 mL). The separated organic layer was
dried (Na2SO4) and the solvent was concentrated in vacuo. The
crude residue was chromatographed (silica gel, PE–EtOAc, 95:0.5)
to give 11 as a white solid; yield: 0.54 g (96%); mp 52–54 °C (Lit.15
54–56 °C).
[a]D25 –15.21 (c 1.04, CHCl3) [Lit.15 [a]D20 –15.4 (c 1.04, CHCl3)].
IR (CHCl3): 2984, 1746 cm–1.
1H NMR (200 MHz, CDCl3): d = 1.28 (t, J = 7.2 Hz, 3 H), 1.39–1.56
(m, 21 H), 3.89–3.97 (m, 1 H), 4.04–4.20 (m, 4 H), 4.9 (d, J = 6.2
Hz, 1 H), 4.27–4.32 (m, 1 H).
All reactions were carried out under argon or N2 in oven-dried
glassware using standard gas-light syringes, cannulas, and septa.
Solvents and reagents were purified and dried by standard methods
prior to use. The progress of all the reactions was monitored by TLC
using aluminum plates precoated with silica gel 60 F254 (0.25 mm,
Merck). Column chromatography was performed on silica gel (60–
120 mesh) using petroleum ether–EtOAc mixtures as the eluent. Pe-
troleum ether (PE) refers to the fraction with bp 60–80 °C. Optical
rotations were measured on a Jasco DIP-360 digital polarimeter at
25 °C. IR spectra were recorded on a Perkin-Elmer FT-IR spectro-
photometer. 1H and 13C NMR spectra were recorded on Bruker AC-
200, AC-400, and AC-500 spectrometer at 200 MHz, 400 MHz, or
500 MHz (1H) and at 50 MHz, 100 MHz, or 125 MHz (13C) with
CDCl3 as internal standard. ESI-MS were obtained using an API-Q-
Star Applied Biosystems spectrometer. Elemental analysis was car-
ried out on a Carlo Erba CHNSO analyzer.
13C NMR (50 MHz, CDCl3): d = 14.1, 25.8, 27.0, 28.2, 59.4, 61.1,
65.2, 78.7, 80.5, 93.9, 94.5, 110.5, 111.2, 153.1, 170.8.
MS (ESI): m/z = 396 (M+ + Na), 411.9 (M+ + K).
(2S,3S)-3-[(S)-3-(tert-Butoxycarbonyl)-2,2-dimethyloxazolidin-
4-yl]-2,3-(isopropylidenedioxy)propan-1-ol (12)
To a soln of LiAlH4 (0.23 g, 6.1 mmol) in anhyd THF (20 mL) was
added a soln of ester 11 (1.5 g, 4.04 mmol) in anhyd THF at 0 °C
through a syringe and resulting mixture was stirred at r.t. for 1 h
(TLC showed complete consumption of starting material). The mix-
ture was quenched with sat. aq Na2SO4 soln (0.2 mL) at 0 °C and
then filtered through a Celite pad and the filtrate was concentrated.
The crude residue was purified by column chromatography (silica
gel, PE–EtOAc, 8:2) to give 12 as a colorless oil; yield: 1.0 g (75%).
Ethyl (E)-3-[(R)-3-(tert-Butoxycarbonyl)-2,2-dimethyloxazoli-
din-4-yl]propenoate (8)
To a soln of Ph3P=CHCO2Et (1.83 g, 5.24 mmol) in anhyd THF (15
mL) was added a soln of freshly prepared Garner’s aldehyde 9 (0.8
g, 3.45 mmol) in anhyd THF (5 mL). The mixture was stirred at 60
°C for 5 h. It was then concentrated and purified by column chro-
matography (silica gel, PE–EtOAc, 9.5:0.5) to give 8 as a yellow
oil; yield: 0.94 g (90%).
[a]D25 –22 (c 0.8, CHCl3).
[a]D25 –44.02 (c 1.09, CHCl3) [Lit.15 [a]D20 –44.3 (c 1.09, CHCl3)].
IR (CHCl3): 3500, 2938 cm–1.
IR (CHCl3): 1712 cm–1.
1H NMR (400 MHz, CDCl3): d = 1.37–153 (m, 21 H), 2.38 (br s, 1
1H NMR (200 MHz, CDCl3): d = 1.26 (t, J = 7.08 Hz, 3 H), 1.40–
1.61 (m, 15 H), 3.74–3.80 (m, 1 H), 4.03–4.11 (m, 1 H), 4.16 (q,
J = 7.2 Hz, 2 H), 4.39–4.52 (m, 1 H), 5.87 (d, J = 15.4 Hz, 1 H),
6.75–6.86 (m, 1 H).
13C NMR (50 MHz, CDCl3): d = 13.5, 25.1, 28.2, 60.5, 65.7, 72.3,
80.2, 105.5, 121.2, 137.1, 150.5, 165.8.
H), 3.52 (m, 1 H), 3.73–3.92 (m, 3 H), 4.06–4.26 (m, 3 H).
13C NMR (100 MHz, CDCl3): d = 24.2, 26.8, 28.1, 58.9, 62.0, 65.2,
79.2, 80.6, 93.7, 108.2, 153.0.
Anal. Calcd for C16H29NO6: C, 57.99; H, 8.82; N, 4.23. Found: C,
58.04; H, 8.90; N 4.26.
Ethyl (2R,3S)-3-[(S)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-
oxazolidin-4-yl]-2,3-dihydroxypropanoate (7)
(2S,3S)-3-[(S)-3-(tert-Butoxycarbonyl)-2,2-dimethyloxazolidin-
4-yl]-2,3-(isopropylidenedioxy)-1-(mesyloxy)propane (6)
To a mixture of K3Fe(CN)6 (6.94 g, 21.1 mmol), K2CO3 (2.91 g,
21.1 mmol), and (DHQ)2PHAL (60 mg, 1 mol%) in t-BuOH–H2O
(1:1, 35 mL) cooled to 0 °C was added 1 M OsO4 in toluene (0.3
mL, 0.4 mol%) followed by MsNH2 (0.7 g, 7.02 mmol). The mix-
ture was stirred at 0 °C for 5 min and then the olefin 8 (2.10 g, 7.02
mmol) was added in one portion. The mixture was stirred at 0 °C for
24 h and then quenched with solid Na2SO3 (10.5 g). Stirring was
continued for an additional 45 min, and then the soln was extracted
To a soln of alcohol 12 (0.6 g, 1.81 mmol) in anhyd CH2Cl2 (5 mL)
at 0 °C was added Et3N (0.4 mL, 2.72 mmol). The mixture was
stirred for 10 min, MsCl (0.2 mL, 2.17 mmol) and DMAP (0.27 g,
2.72 mmol) were added and resulting mixture was stirred at 0 °C for
2 h (TLC showed complete consumption of starting material). The
mixture was quenched with ice pieces and extracted with CH2Cl2
(3 × 15 mL), then washed with brine (10 mL), dried (Na2SO4), and
concentrated. The crude residue was purified by column chroma-
Synthesis 2010, No. 18, 3063–3066 © Thieme Stuttgart · New York

3066
P. K. Upadhyay, P. Kumar
FEATURE ARTICLE
tography (silica gel, PE–EtOAc, 9:1) to give 6 as a white sticky
compound; yield: 0.6 g (81%).
(8) Kiciak, K.; Jacobsson, U.; Golebiowski, A.; Jurczak, J. Pol.
J. Chem. 1993, 67, 685.
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1990, 1, 119. (b) Hosaka, A.; Ichikawa, S.; Shindo, H.; Sato,
T. Bull. Chem. Soc. Jpn. 1989, 62, 797. (c) Mulzer, J.;
Becker, R.; Brunner, E. J. Am. Chem. Soc. 1989, 111, 7500.
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Tetrahedron Lett. 1986, 27, 4536. (e) Zanardi, F.; Battistini,
L.; Nespi, M.; Rassu, G.; Spanu, P.; Cornia, M.; Casiraghi,
G. Tetrahedron: Asymmetry 1996, 7, 1167. (f) Fleet, G. W.
J.; Son, J. C. Tetrahedron 1988, 44, 2637. (g) Weir, C. A.;
Taylor, C. M. J. Org. Chem. 1999, 64, 1554. (h) Chen, S.
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H. Synlett 1999, 614. (k) Kim, I. S.; Zee, O. P.; Jung, Y. H.
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Lett. 1998, 39, 5743. (c) Arakawa, Y.; Yoshifuji, S. Chem.
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S. F.; Smith, M. E. B.; Turner, N. J. Tetrahedron Lett. 2000,
41, 4481. (e) Hulme, A. N.; Montgomery, C. H.; Henderson,
D. K. J. Chem. Soc., Perkin Trans. 1 2000, 1837. (f) Huwe,
C. M.; Blechert, S. Synthesis 1997, 61. (g) Goli, D. M.;
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1H NMR (500 MHz, CDCl3): d = 1.38 (s, 6 H), 1.47–1.53 (m, 15 H),
3.03 (s, 3 H), 3.84 (t, J = 8.5 Hz, 1 H), 3.90–3.93 (m, 1 H), 4.06–
4.15 (m, 3 H), 4.32 (d, J = 11.3 Hz, 1 H), 4.52 (br s, 1 H).
13C NMR (125 MHz, CDCl3): d = 26.9, 27.0, 28.3, 37.7, 62.3, 69.1,
75.6, 80.3, 110.1, 120.0, 155.8.
(2S,3S,4S)-2-(Hydroxymethyl)pyrrolidine-3,4-diol (1)
To a soln of mesylate 5 (0.1 g, 0.24 mmol) in EtOAc (2.0 mL) was
added 2 M HCl (0.05 mL, 0.61 mmol) at 0 °C and the reaction mix-
ture was stirred for 3 h. The mixture was neutralized to pH 8 with
sat. NaHCO3 soln (1.0 mL) and stirred for 1 h. The mixture was ex-
tracted with EtOAc (3 × 10 mL), then the combined extracts were
dried (Na2SO4) and concentrated. The crude compound was puri-
fied by flash column chromatography (silica gel, CH2Cl2–MeOH,
1:1) to give 1 as a pale yellow oil; yield: 22 mg (69%).
[a]D25 –11.4 (c 0.2 MeOH) [Lit.11f [a]D25 –12.0 (c 0.21 MeOH)].
1H NMR (500 MHz, CD3OD): d = 3.17–3.52 (m, 3 H), 3.67–3.72
(m, 4 H), 3.87 (m, 4 H).
13C NMR (125 MHz, CD3OD): d = 54.4, 66.8, 77.7, 78.0, 78.2.
Acknowledgement
P.K.U. thanks CSIR New Delhi for the award of Senior Research
Fellowship. The financial assistance from DST, New Delhi (Grant
No. SR/S1/ OC-40/2003) is gratefully acknowledged.
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Tetrahedron Lett. 1985, 26, 3125. (b) Dhavale, D. D.;
Kumar, K. S. A.; Chaudhari, V. D.; Sharma, T.; Sabharwal,
S. G.; Reddy, J. P. Org. Biomol. Chem. 2005, 3, 3720.
(c) Sugiyama, M.; Hong, Z.; Liang, P.-H.; Dean, S. M.;
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