Toward the Development of a General Chiral Auxiliary. Enantioselective Alkylation and a New Catalytic Asymmetric Addition of Silyloxyfurans: Application to a Total Synthesis of (‐)‐Rasfonin

Boeckman, Robert K.; Pero, Joseph E.; Boehmler, Debra J.

doi:10.1002/chin.200703200

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“…39 After the pioneering work of Figadere, 36−39 several catalytic systems involving both metal-based catalysts and organocatalysts have emerged for the effective asymmetric vinylogous aldol reaction (VMAR) between TMSOF 1 and a range of aldehydes (Figure 3). 40−47 The resulting chiral γ-butenolides have been elegantly employed as key building blocks for instance in the total syntheses of (−)-rasfonin 48 (Scheme 5) and (+)-azaspiracid-1 49 (Scheme 6). Since the VMAR of silyl dienolates and aldehydes has been comprehensively documented and reviewed by Denmark, 24 Casiraghi, 33,35 and others, 25,34 the emphasis of this part is based on recent progress in the use of substituted αketoesters as electrophiles for the catalytic asymmetric VMAR.…”

Section: Furanone-derived Enolates As Nucleophiles 21 Asymmetric Aldo...mentioning

confidence: 99%

Catalytic Asymmetric Synthesis of Butenolides and Butyrolactones

2017

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γ-Butenolides, γ-butyrolactones, and derivatives, especially in enantiomerically pure form, constitute the structural core of numerous natural products which display an impressive range of biological activities which are important for the development of novel physiological and therapeutic agents. Furthermore, optically active γ-butenolides and γ-butyrolactones serve also as a prominent class of chiral building blocks for the synthesis of diverse biological active compounds and complex molecules. Taking into account the varying biological activity profiles and wide-ranging structural diversity of the optically active γ-butenolide or γ-butyrolactone structure, the development of asymmetric synthetic strategies for assembling such challenging scaffolds has attracted major attention from synthetic chemists in the past decade. This review offers an overview of the different enantioselective synthesis of γ-butenolides and γ-butyrolactones which employ catalytic amounts of metal complexes or organocatalysts, with emphasis focused on the mechanistic issues that account for the observed stereocontrol of the representative reactions, as well as practical applications and synthetic potentials.

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