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K. Singhal and A. Kumar
O
H 3 C
CH 3 C
O
C
H 3 C
OH
CH 3
O
O
O
H 3 C
CH 3 C
HO
OH
CH 3
O
F
HO
(i) NaOBr
(ii) CH 3 COOK
(iii) HF
H 3 C
CH 3 C H
O
AcO
(i) MeMgBr, (ii)H 2 , (iii) Ac 2 O,(iv) MCPB, (v) OH
- ,
(vi) Br 2 ,(vii)NaOAc/KI, (viii)CrO 3 , Py (ix) DMF
(x) Biotransformation, (xi)TsCl, (xii)NaOAc
(xiii) AcNHBr/H 3 O
+ , (xiv) OH
-
, (xv) HF
C 22 H 29 FO 5
O
H 3 C
CH 3 C CH 3
O
O
HO
(i) Corynebacterium simplex (ATCC 6946)
(ii) Cr, HCl, (iii) MsCl, Et 3 N, AcONa, AcOH,
(iv) NBS, HClO 4 , Acetone, (v)K 2 CO 3 , MeOH,
(iv)MeMgCl, CuCl, THF, O 2 , (MeO) 3 P, DMF,
(vii) HF, DMF, (viii)I 2 , CaCl 2 , CaO, MeOH,
AcOK, AcOH, Acetone, (ix) K 2 CO 3 , MeOH
O
H 3 C
CH 3 C CH 3
OH
CH 3
O
(i) Br 2 , HCl, MeOH,(ii) AcONa, HSO 4 NBu 4 ,
AcOEt, (iii) Ca(ClO)2, AcOH, (iv) Br2, HBr,
AcOH, Dioxane, (v) CaCO3, LiBr,
dimethylacetamide, (iv)Rhizopus nigricans
fermentation, (vii) Ethylchloroformate,Et 3 N,
DCM, (viii) PCl 5 , THF, -90
o C (ix) DDH, HClO 4 ,
DMF, (x) NaOH, MeOH, DCM, 0
o C, (xi)HF, DMF.
(d)
(b)
(c)
O
H 3 C
CH 3 C
OH
O
HO
(a)
OAc
CH 3
(e)
(i)MsCl
(ii) HOBr, NaOH, HF?THF
O
DMs
Scheme 16.1 Different chemical methods for DMs synthesis
Fig. 16.4 Inhibition of SARS-coV-2 infection via green synthesized DMs analogue