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ChemInform Abstract: Lewis Acid Assisted Vinylogous Mannich and Mukaiyama Aldol Reactions: A Route to Densely Hydroxylated Indolizidine Alkaloid Analogues.

✍ Scribed by Gloria Rassu; Paola Carta; Luigi Pinna; Lucia Battistini; Franca Zanardi; Domenico Acquotti; Giovanni Casiraghi

Publisher: John Wiley and Sons
Year: 2010
Weight: 35 KB
Volume: 30
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199936258

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✦ Synopsis

Reactions: A Route to Densely Hydroxylated Indolizidine Alkaloid Analogues.

-The synthesis of hydroxymethyl-substituted indolizidine alkaloid analogues (IX) and (X) on similar ways is presented, involving vinylogous Mukaiyama aldol condensation of pyrrole-based silyloxydiene (I) with protected (S)-glyceraldehyde (II) and SnCl 4 -mediated vinylogous Mannich reaction of the derived 2-methoxypyrrolidine (IV) with silyloxyfuran (V) as key steps. -

📜 SIMILAR VOLUMES

Lewis Acid Assisted Vinylogous Mannich a

Lewis Acid Assisted Vinylogous Mannich and Mukaiyama Aldol Reactions: A Route to Densely Hydroxylated Indolizidine Alkaloid Analogues

✍ Gloria Rassu; Paola Carta; Luigi Pinna; Lucia Battistini; Franca Zanardi; Domeni 📂 Article 📅 1999 🏛 John Wiley and Sons 🌐 English ⚖ 276 KB

The hydroxymethyl-substituted indolizidines 6 and 7, scantily exploited vinylogous version of the Mannich reaction. The key iminium electrophilic acceptor 11 is, in representative members of a ring-B-expanded alexineaustraline subclass, are readily accessible by starting with turn, available through