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ChemInform Abstract: Synthetic Approaches to Rapamycin. Part 2. A Synthesis of a C21-C42 Fragment.

โœ Scribed by M. NORLEY; P. KOCIENSKI; A. FALLER

Publisher
John Wiley and Sons
Year
2010
Weight
32 KB
Volume
28
Category
Article
ISSN
0931-7597

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โœฆ Synopsis

Synthetic Approaches to Rapamycin. Part 2. A Synthesis of a C21-C42 Fragment.

-The synthesis of the C21-C42 fragment (XI) of the highly cytotoxic and potent immunosuppressive rapamycin is performed by coupling of the sub-fragments (VIII)-(X). Highlights of the preparation are the introduction of the C27/C28 stereochemistry in (VIII) by a sigmatropic (3,3)-Ireland-Claisen rearrangement with use of a furylsilane as the latent silyloxy group.

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ChemInform Abstract: Toward a Total Synt
ChemInform Abstract: Toward a Total Synthesis of Pristinamycin IIB; a Chiron Approach to a C-9/C-16 Fragment.
โœ P. BREUILLES; D. UGUEN ๐Ÿ“‚ Article ๐Ÿ“… 2010 ๐Ÿ› John Wiley and Sons โš– 39 KB ๐Ÿ‘ 2 views

Toward a Total Synthesis of Pristinamycin II B ; a Chiron Approach to a C-9/C-16 Fragment. -Starting from readily available (S)-malic acid derivative (I), an appreciable amount (ca. 2 g) of the title fragment (XV) is prepared using the Grignard reaction of the propargyl diol (VI) as the key step. T