An efficient synthesis of 4-ethyl-4-[(3-hydroxycarbonyl)propyl]dihydro-2(3 H)-furanone and its use in a formal total synthesis of (±)-quebrachamine

The Rh 2(OAc) 4-catalyzed reaction of diazoacetate 5 provides ready access to the pivotal cyclic acetal 13 that undergoes Pictet-Spengler-type condensation with tryptamine to directly afford an epimeric mixture of the tetracyclic lactam 17a,b. Lithium aluminum hydride reduction of 17a,b provides the...

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Bibliographic Details
Published inTetrahedron Vol. 54; no. 44; pp. 13435 - 13448
Main Authors Wee, Andrew G.H., Yu, Qing
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 29.10.1998
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALCOHOLS
INSERTION
LACTONES
QUATERNARY CARBON CENTERS
CONSTRUCTION
ALKALOIDS
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Summary:The Rh 2(OAc) 4-catalyzed reaction of diazoacetate 5 provides ready access to the pivotal cyclic acetal 13 that undergoes Pictet-Spengler-type condensation with tryptamine to directly afford an epimeric mixture of the tetracyclic lactam 17a,b. Lithium aluminum hydride reduction of 17a,b provides the known tetracyclic amino alcohol 18a,b which, overall, constitutes a formal synthesis of (±)-quebrachamine. The key intermediate 13 was derived from the γ-lactone 12 that was efficiently prepared via the dirhodium(II)-carbenoid mediated tertiary CH insertion of the appropriate diazoester. Reaction of 13 with tryptamine gave, after reduction, the known tetracycle 18.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(98)00825-4