- A total synthesis of (+/-)-biotin
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A total synthesis of (+/-)-biotin 1 based on the photochemical cycloaddition raection of 1,3-diacetylimidazolin-2-one 2 with 3,4-dihydro-2-methoxy-2H-pyran 3 is described.The photoadduct 4 was converted into the lactone 6, which bears the complete carbon framework and all the requisite stereochemical features, via hydrolysis, Wittig olefination, and catalytic hydrogenation to the cyclobutanol 5 followed by oxidative rearrangement.Subsequent conversion of the lactone to (+/-)-biotin followed from literature precedent (5).
- Whitney, Ralph Allen
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p. 1158 - 1160
(2007/10/02)
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- SYNTHESIS OF (+-)-BIOTIN FROM A SUBSTITUTED 2,3-DEHYDROTHIOPHANE
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(+-)-Biotin has been synthesized from a mixture of cis- and allo-trisubstituted dehydrothiophanes by a scheme providing for the easy elimination of the accompanying allo-substituted thiophane in the form of an intermediate and not as the final isomeric allo-biotin.The imidazoline ring of biotin is formed from a dialkoxycarbonyldiaminothiophane under the conditions of partial hydrolysis of one of the protective groups with the elimination of phosgene from the scheme of synthesis.
- Mikhano, S. D.,Kulachkina, N. S.,Filippova, T. M.,Suchkova, I. G.,Berezovskii, V. M.
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p. 176 - 178
(2007/10/02)
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- Olefinic Nitrone and Nitrile Oxide Cycloadditions. A Short Stereospecific Synthesis of Biotin from Cycloheptene
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A novel synthesis of biotine (6) from cycloheptene (4) via the key amino alcohol 5 is described.The synthetic scheme is based upon an intramolecular nitrone-olefin cycloaddition of the reactive intermediate 13, generated in situ from the aldehyde
- Confalone, Pat N.,Pizzolato, Giacomo,Confalone, Dianne Lollar,Uskokovic Milan R.
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p. 1954 - 1960
(2007/10/02)
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