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ChemInform Abstract: Novel Route to the Synthesis of Hydroxylated Pyrrolidine Derivatives via the Intramolecular Reaction of γ-Aminoallylstannane with Aldehyde. Total Synthesis of (+)-Preussin.

✍ Scribed by I. KADOTA; S. SAYA; Y. YAMAMOTO

Publisher
John Wiley and Sons
Year
2010
Weight
37 KB
Volume
29
Category
Article
ISSN
0931-7597

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✦ Synopsis

Novel Route to the Synthesis of Hydroxylated Pyrrolidine Derivatives via the Intramolecular Reaction of γ-Aminoallylstannane with Aldehyde. Total Synthesis of (+)-Preussin. -Contrary to Lewis acid mediated reaction, the thermal cyclization of γ-amino allylstannane (I) having an aldehyde group gives the cis-β-hydroxypyrrolidine (II) as the sole product. Application of these conditions to the chiral allylstannane (IV) provides the separable diastereomers (VI) and (VII). The latter is a precursor for the synthesis of (+)-preussin (VIII). -(KADOTA, I.

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