- SYNTHETIC PROCESS FOR PREPARATION OF MACROCYCLIC C1-KETO ANALOGS OF HALICHONDRIN B AND INTERMEDIATES USEFUL THEREIN INCLUDING INTERMEDIATES CONTAINING -SO2-(P-TOLYL) GROUPS
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Disclosed is a compound of formula 1, or a pharmaceutically acceptable salt thereof, where R1, R2, R3, R4, R5, R6, R7, R7', R8, R9, R10, R11, R12 and R13 are as disclosed herein. Also, disclosed is a process for the preparation of the compound of formula 1, or a pharmaceutically acceptable salt thereof, and intermediates used therein. The compound of formula 1 can be used in the preparation of halichondrin analogs, such as Eribulin; and a process for its preparation from the compound of formula 1 is also disclosed.
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- Early introduction of the amino group to the C27-C35 building block of Eribulin
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A new synthetic strategy towards the C27-C35 subunit of Eribulin (1) has been devised to include a protected 1,2-amino alcohol at C34-C35. Early introduction of the C35 amino group in the synthesis of 1 increases the efficiency of the route. This new approach can be accomplished on a multi-gram scale and allows for the successful synthesis of Eribulin.
- Rudolph, Alena,Alberico, Dino,Jordan, Robert,Pan, Ming,Souza, Fabio E.S.,Gorin, Boris
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p. 7059 - 7061
(2013/12/04)
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- Rh2(II)-catalyzed nitro-group migration reactions: Selective synthesis of 3-nitroindoles from β-nitro styryl azides
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Rhodium carboxylate complexes (1 mol %) catalyze the migration of electron-withdrawing groups to selectively produce 3-substituted indoles from β-substituted styryl azides. The relative order of migratorial aptitude for this transformation is ester ? amide H sulfonyl benzoyl ? nitro.
- Stokes, Benjamin J.,Liu, Sheng,Driver, Tom G.
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supporting information; experimental part
p. 4702 - 4705
(2011/05/16)
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- (Alkoxyallyl)sulfones as enal β-anion equivalents. Synthesis of 5-substituted 2(5H)-furanones
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2(5H)-Furanones 14 may be prepared in a four-step sequence starting from (alkoxyallyl)sulfone 10 and aldehydes.
- Craig, Donald,Etheridge, Christopher J.,Smith, Alison M.
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p. 15267 - 15288
(2007/10/03)
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- 1-Benzyloxy-3-(p-tolylsulfonyl)propene as an acrolein β-anion equivalent. Synthesis of 4-substituted 2-butenolides
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Lithiation of 1-benzyloxy-3-(p-tolylsulfonyl)propene 6 and reaction with aldehydes give alcohols 7. Sequential hydrolysis-cyclization, oxidation and DBU-mediated elimination of dine elements of p-TolSO2H gives 4-substituted 2-butenolides 10 in good overall yield.
- Craig, Donald,Etheridge, Christopher J.,Smith, Alison M.
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p. 7445 - 7446
(2007/10/02)
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