A unified and common intermediate strategy for the asymmetric total synthesis of 3-deoxy-neo-inositol and conduritol E

Article abstract of DOI:10.1016/j.tetlet.2016.06.127

A competent, simplistic, and unified synthetic approach has been outlined for enantiomerically pure 3-deoxy-neo-inositol and conduritol E starting from D-ribose via a common chiral cyclohexenol derivative. The focal attributes of the synthetic route inclu

Full text of DOI:10.1016/j.tetlet.2016.06.127

Accepted Manuscript
A unified and common intermediate strategy for the asymmetric total synthesis
of 3-deoxy-neo-inositol and conduritol E
Amarendra Panda, Rayhan Gafur Biswas, Shantanu Pal
PII:
S0040-4039(16)30806-1
DOI:
http://dx.doi.org/10.1016/j.tetlet.2016.06.127
TETL 47854
Reference:
Tetrahedron Letters
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Revised Date:
Accepted Date:
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27 June 2016
28 June 2016
Please cite this article as: Panda, A., Biswas, R.G., Pal, S., A unified and common intermediate strategy for the
asymmetric total synthesis of 3-deoxy-neo-inositol and conduritol E, Tetrahedron Letters (2016), doi: http://
dx.doi.org/10.1016/j.tetlet.2016.06.127
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A unified and common intermediate strategy for the
asymmetric total synthesis of 3-deoxy-neo-inositol and
conduritol E
Amarendra Panda, Rayhan Gafur Biswas and Shantanu Pal*

1
Tetrahedron Letters
journal homepage: www.els evier.com
A unified and common intermediate strategy for the asymmetric total synthesis of 3-
deoxy-neo-inositol and conduritol E
Amarendra Panda, Rayhan Gafur Biswas and Shantanu Pal*
Organic Chemistry Laboratory, School of Basic Sciences, Indian Institute of Technology Bhubaneswar, Bhubaneswar, Orissa
751007, India.
ARTICLE INFO
ABSTRACT
Article history:
Received
A competent, simplistic and unified synthetic approach has been outlined for enantiomerically
pure 3-deoxy-neo-inositol and conduritol E starting from D-ribose via a common chiral
cyclohexenol derivative. The focal attributes of the synthetic route include stereoselective
Grignard reaction, Wittig olefination, ring closing metathesis (RCM) and cis dihydroxylation.
Received in revised form
Accepted
Available online
2009 Elsevier Ltd. All rights reserved.
Keywords:
3-Deoxy-neo-inosotol
Conduritol E
Asymmetric synthesis
Common intermediate
Carbocycles
Polyhydroxy-cycloalkanes/alkenes belong to a large and supreme
family of natural products known as the cyclitols.1 Synthetic
approaches to naturally occurring cyclitols and their analogues
are of great significance due to their diverse biological properties,
versatility as synthetic intermediates for many biologically
imperative molecules and natural products and the structural
challenges inherent in their syntheses.2 The conduritols3 and the
inositols4 are the cyclitol derivatives that evince prominently in
numerous biological processes. The conduritol comprises of six
diastereomers which are designated as A to F. The existence of
four stereogenic C-atoms allows them to prevail in six different
configurations, out of these two are meso compounds (conduritol
A and D) while the remaining four are enantiomeric pairs
(conduritol B, C, E and F). Conduritol A and F occur naturally
(Figure 1). The conduritols and their derivatives have been found
to possess interesting biological properties such as antibiotic,
antileukemic, antifeedant, tumor inhibitory, glycosidase
inhibitory and growth regulating activities etc.5 Epoxyconduritols
and aminoconduritols act as inhibitors of glycosidases6 while the
cyclophellitols have been proven to be potent inhibitors of HIV
infection.7 The conduritol A analogues regulate the insulin
pathways,10 several deoxy inositols have also been used for
glycosidase inhibition and mediation of cellular
communication.11
The attention in conduritols and related cyclitols has been
amplified and continues to attract considerable importance due to
synthetic challenge and a range of useful biological activities
exhibited by them. In addition, the multifunctional nature and the
stereochemical complexity of cyclitols and derivatives have made
them convenient and versatile intermediates in chemical
syntheses of several related natural products and biologically
impressive
molecules
such
as
aminoconduritols,12
conduritolepoxides,13 cyclophellitol,14 pseudosugars,15 aminosugar
analogues,16 etc. Hence, the stereocontrolled synthesis of this
class of compounds has been stimulating considerable efforts
since last few decades.17 In fact, due to the presence of several
stereogenic centers in the cyclohexane moiety, many of these
syntheses resulted in racemic mixtures. The general drawbacks of
such methods is that, they often provide diastereomeric mixtures
and lack of proper stereogenic orientation. Although several
synthetic approaches to conduritols and related cyclitols have
been published17 till date, some of those have reported the use of
chiral catalysts, diastereoselective catalysts, and enzymatic
resolution18 to achieve enantiomerically pure compounds while
other few have employed chiral-pool strategies.19 Still the
emerging demand for this class of compounds instigates further
synthetic work aimed at improving the preparative efficiency and
achieving high degrees of stereo and regio control.
liberation
from isolated pancreatic islets with varying
concentrations of glucose.8 Similarly, the inositols are
1,2,3,4,5,6-cyclohexanehexols and can exist as nine stereo-
isomers: myo, scyllo, cis, D-(+)-chiro, L-(-)-chiro, epi, allo, muco
and neo inositols (Figure 1). Among these the D-(+)-chiro and L-
(-)-chiro are enantiomers of each other, rest of them are optically
inactive having plane of symmetry and myo, scyllo, cis, D-(+)-
chiro, L-(-)-chiro are naturally occurring inositols. The inositols
as well as their structural variants like quercitols, deoxyinositols
have prominent biological properties.9 Moreover, inositol
phosphate derivatives mediate intracellular signal transduction
In this context, leveraged by the growing interest in
conduritols and related cyclitols with potential biological activity,
herein, we report a unified and common intermediate strategy for
the asymmetric total synthesis of 3-deoxy-neo inositol and

2
Tetrahedron
conduritol-E from a readily available inexpensive starting
material D-ribose via stereoselective Grignard reaction, Wittig
olefination, ring closing metathesis (RCM) and cis
dihydroxylation as key steps. The cornerstone of the synthetic
approach has been delineated retrosynthetically in figure 2.
deprotection. On the other hand, conduritol E 1 was speculated to
be derived from the same cyclohexenol 6 by couple of more
trasformations like syn dihydroxylation, protection, elimination
and acetonide hydrolysis respectively. The key cyclohexenol 6,
in turn could be obtained from diene 7 via RCM reaction. The
diene 7 was predicted to be synthesized from lactol 8 by Wittig
olefination and the lactol 8 could be prepared from D-ribose 9 by
acetonide protection, Grignard reaction followed by oxidative
cleavage of vicinal diols.
In order to pursue the theme delineated in figure 2, the key
cyclohexinol
6 was initially attempted for its synthesis
commencing from D-ribose 9 by a few steps. D-ribose was treated
with anhydrous acetone in presence of a catalytic amount of
concentrated sulfuric acid to give the corresponding 2,3-
acetonide protected diol 10. Then the lactol 10 was subjected to
From the above retrosynthetic analysis, it was envisaged that
both conduritol E 1 and 3-deoxy-neo-inositol 2 could be
synthesized from a common intermediate 6 by implementing the
following steps of reaction. 3-deoxy-neo-inositol
2 was
contemplated to be synthesized from the key cyclohexenol 6 by
syn dihydroxylation with OsO4 and followed by acetonide

3
srereoselective Grignard reaction with allylmagnesium bromide
in anhydrous ether to afford the ring opened polyhydroxylated
20
olefin 11 predominantly over the other diastereomer (Scheme
1). The stereoselectivity of Grignard reaction might be explained
via the Felkin-Anh cyclic chelate transition model as shown in
(Figure 3).21 This chelate transition state articulates the β-attack
of nucleophile from the less hindered face providing a single
stereoisomer in an exclusive amount. The oxidative cleavage of
the vicinal diol in compound 11 was carried out by sodium meta
periodate in dichloromethane to obtain the desired lactol 8 in
84% yield. Wittig olefination of lactol
8 with methyl
triphenylphosphonium ylide in presence of potassium-tert-
butoxide exhibited the diene 7 in a good yield which established
the platform for ring closing metathesis22 to fabricate
cyclohexene scaffold. The key cyclohexenol 6 was achieved
smoothly by ring closing metathesis reaction of diene 7 with
Grubbs’ second generation catalyst (Scheme 1).
The cyclohexenol 6 was first protected to its mesylate 15 by
mesyl chloride in presence of Et3N in dichloromethane. Then the
mesylate compound 15 was subjected to cis didydroxylation by
OsO4 to give the diol compound 16 in very good yield. The diol
16 was easily protected by 2, 2 dimethoxypropane in THF to
supply the desired diacetonide compound 17 in a good yield.
Further, the exposure of diacetonide 17 to potassium-tert-
butoxide (t-BuO− K+) resulted the elimination of mesylate group
to deliver the protected conduritol E 3. The removal of both the
acetonide group by acidic hydrolysis using TFA afforded the
desired (+)-condurirol E 1 in very good yield as shown in scheme
4. All the synthesized compounds were thoroughly characterized
1
by IR, H NMR, 13C NMR, HRMS, melting point, etc. The exact
stereochemistry of both 3 deoxy-neo-inositol and (+)-conduritol
E was further reconfirmed by the X-ray crystal structure of the
diol intermediate 16 (figure 4).
A simple, orthodox transformation was intended for the
accomplishment of total synthesis of 3- deoxy-neo-inositol 2
from the hexenol derivative 6. Syn dihydroxylation23 of alkene in
compound 6 was successfully attained by OsO4 in presence of N-
methylmorpholine N-oxide (NMO) to acquire the desired triol 12
as a sole product with high selectivity. This stereochemical
predilection might be governed by the existence of the acetonide
group at the α face of the cyclohexenol. Finally, the acetonide
deprotection of triol 12 with trifluroacetic acid in THF-water
(1:1) furnished 3-deoxy-neo-inositol 2 in 79% yield (Scheme 2).
In order to execute the total synthesis of conduritol E, the triol
12 was initially strived for acetonide protection to obtain the
diacetonide protected compound 13. However, the protection led
to the formation of two regioisomers 13 (trace amount) and
undesired isomer 14 as a major product (Scheme 3). At this
juncture, it was almost impossible to proceed further by this
synthetic route. Hence, to circumvent the aforementioned draw
back, the strategy was rehabilitated accordingly for the total
synthesis of conduritol E.
Figure 4. ORTEP of compound 16 (drawn at 50% probability)

4
Tetrahedron
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a
common chiral cyclohexenol
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been endeavored featuring stereoselective Grignard reaction,
Wittig olefination, ring closing metathesis (RCM) and cis
dihydroxylation as the key steps for achieving the total syntheses.
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Acknowledgements
This work was supported by the Department of Science and
Technology (DST), India, FAST track Project Grant No:
SERB/F/0287. We thank CIF at IIT Bhubaneswar for NMR and
X-ray crystallographic data.
Supplementary data
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Supplementary data (experimental details and characterization
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--------------------------------------------------------------------------------
*Corresponding authors Email: spal@iitbbs.ac.in, Fax: +91-
674-2301983, Tel: +91-674-2576054

6
Tetrahedron
Highlights
•
•
•
Asymmetric total synthesis of 3-deoxy-
neo-inositol and conduritol E via a
common intermediate
Stereoselective
Grignard
reaction,
Wittig olefination, RCM reaction and
cis dihydroxylation
Functionalized polyhydroxylated six-
membered carbocycles

7
A unified and common intermediate
strategy for the asymmetric total
synthesis of 3-deoxy-neo-inositol and
conduritol E
Amarendra Panda, Rayhan Gafur Biswas and
Shantanu Pal*
Organic Chemistry Laboratory, School of Basic Sciences,
Indian Institute of Technology Bhubaneswar, Bhubaneswar,
Orissa 751007, India.
*Email: spal@iitbbs.ac.in Fax: +91-674-2301983, Tel: +91-
674-2576054
OH
HO
HO
OH
HO
O
1
OH
OH
D- ribose
OH
conduritol E
HO
O
O
OH
HO
6
HO
OH
OH
2
neo
3-deoxy-
-inositol