Convergent, enantiospecific total synthesis of the novel cyclodepsipeptide (+)-jasplakinolide (jaspamide)

Grieco, Paul A.; Hon, Yung‐Son; Pérez-Medrano, Arturo

doi:10.1021/ja00213a050

Cited by 127 publications

(49 citation statements)

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“…[41,42] 2,4-Disubstituted 3-butyrolactones [43] (Scheme 7) are interesting building blocks for natural product synthesis and have been used, for example, in the synthesis of jasplakinolide. [44] We envisioned constructing these highly versatile structures with three contiguous [c] 10 mol% HG-II and 20 mol% 2,6-dichlorobenzoquinone were used. [d] Conversion, determined by GC-MS.…”

Section: Resultsmentioning

confidence: 99%

Copper‐Catalyzed Asymmetric Allylic Alkylation of Halocrotonates: Efficient Synthesis of Versatile Chiral Multifunctional Building Blocks

et al. 2010

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Abstract:The highly enantioselective synthesis of amethyl-substituted esters is reported in up to 90% yield and up to 99% ee using copper-TaniaPhos as chiral catalyst. The transformation proved scalable to at least 6.6 mmol (1.7 g scale). The products of this transformation have been further elaborated to multifunctional building blocks with a single (branched esters and acids) or multiple stereogenic centers (vicinal dimethyl esters, as well as, hydroxy-or iodosubstituted lactones).

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Section: Resultsmentioning

confidence: 99%

Copper‐Catalyzed Asymmetric Allylic Alkylation of Halocrotonates: Efficient Synthesis of Versatile Chiral Multifunctional Building Blocks

et al. 2010

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“…However, macrolactamization does not have a monopoly, as a few notable examples of macrolactonization have been reported. Thus jasplakinolide (22) was cyclized at point (a) using DCC/DMAP.TFA (79% yield) [159] and using DCC only [160] in 36% yield. It is implied that DMAP.TFA in the former example raises the effective concentration of protons thus catalysing macrolactonization.…”

Section: Cyclodepsipeptidesmentioning

confidence: 99%

The cyclization of peptides and depsipeptides

Davies

2003

Journal of Peptide Science

409

241

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Constricting the peptide backbone into a more defined conformational form through cyclization is an activity evolved in nature and in synthetic work, the latter straddling only the most recent decades. The resulting conformational constraints increase the probability of an optimum response with bio-receptors. The purpose of this review is to highlight developments that have proved to be reasonably efficient in the macrocyclization of linear precursors into cyclic peptides and depsipeptides.

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“…Three novel halogenated metabolites (243)(244)(245) were isolated from the Caribbean sponge Iotrochota birotulata, which is taxonomically far removed from the order Verongida (146).…”

Section: F Other Structural Classesmentioning

confidence: 99%