Selective ring opening cross metathesis of cyclopropenone ketal: a one step synthesis of protected divinyl ketones

Michaut, Mathieu; Parrain, Jean‐Luc; Santelli, Maurice

doi:10.1039/a807064d

Cited by 32 publications

(18 citation statements)

References 19 publications

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“…[70] When the ene-diene 85a (Scheme 27) was engaged in a metathesis reaction in the presence of the catalyst HG, the diene 86 was produced in only 15 % yield, presumably because the ruthenium carbene formed at C10 was unreac- tive. To circumvent this problem, Porco et al used the relay RCM strategy discovered by Parrain, Santelli, et al [71] and developed by Hoye et al [72] The first carbene was formed at the terminal olefin of compound 85b, and RCM furnished the corresponding carbene at C11 (along with cyclopentene), which underwent a second RCM to produce the desired oximidine core 86 in good yield. In this fashion, formation of the stable conjugated carbene at C10 was avoided.…”

Section: Oximidinesmentioning

confidence: 99%

Progress in Metathesis Through Natural Product Synthesis

Prunet

2011

Eur J Org Chem

105

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This article covers case studies in natural product syntheses with comments on various aspects of metathesis reactions and on how the difficulties encountered in these syntheses have led to better understanding of these reactions or to more effective reaction conditions and catalysts. Ring‐closingmetathesis leading to small and medium‐sized rings is discussed, followed by macrocycle formation, asymmetric ring‐closing metathesis, and cross metathesis.

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Section: Oximidinesmentioning

confidence: 99%

Progress in Metathesis Through Natural Product Synthesis

Prunet

2011

Eur J Org Chem

105

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“…Parrain and coworkers described an efficient cascade involving the ring opening of cyclopropene ketal of type 71 followed by CM with a variety of alkenes in the presence of catalyst [Ru]-I for the synthesis of protected divinyl ketones [42]. This sequence was employed by Kozmin and coworkers for the preparation of the linear center portion of bistramide A, a marine metabolite isolated from Lissoclinum bistratum which exhibits potent cytotoxicity against several cell lines [43], as well as for the synthesis of spirofungin A, an inhibitor of isoleucyl-tRNA synthase isolated from Streptomyces violaceusniger Tü [44], and routiennocin, an antibiotic agent extracted from Streptomyces routienii Huang sp.…”

Section: Rom/cmmentioning

confidence: 99%

Cross‐Metathesis in Natural Products Synthesis

Prunet

Grimaud

2010

Metathesis in Natural Product Synthesis

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“…Michaut, Parrain, and Santelli showed that the Grubbs ruthenium complex Gru-I ( Figure 1) efficiently catalyses ROM/CM of cyclopropenone ketal 1 to afford 1,4-divinyl ketone derivative 2 in good yields (Scheme 2). [5] The opening of a strained cyclopropene ketal was later used by Kozmin and co-workers to create key spiroketal domains of some natural products, such as bistramide A, spirofungin A, [6b] and routiennocin.…”

mentioning

confidence: 99%

The Joy and Challenge of Small Rings Metathesis

Grela

2008

Angew Chem Int Ed

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carbenes · cycloisomerization · homogeneous catalysis · metathesisOlefin metathesis (from the Greek word metaqesiz, meaning transposition) is an alkylidene exchange between two reacting fragments mediated by transition-metal alkylidene complexes. [1] Recent decades have seen burgeoning interest in olefin metathesis, resulting in a number of elegant applications. Using this tool, chemists can now efficiently synthesize an impressive range of molecules that only a decade ago required significantly longer and tedious routes.[1] Several types of olefin metathesis have been identified so far; among them, ring-closing metathesis (RCM) and cross-metathesis (CM) have been widely applied in the synthesis of biologically active compounds (Scheme 1). Ring-closing metathesis occurs when a diene undergoes intramolecular metathesis to afford a cyclic olefin. Analogous intramolecular reaction of an enyne is sometimes called enyne cycloisomerization or enyne RCM.[2] Ring-closing metathesis of dienes and enynes represent an attractive and powerful tool for the formation of medium and large cycles (! 5-membered rings). However, it is generally acknowledged that small (three-and fourmembered) and strained rings cannot be formed by RCM.

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Selective ring opening cross metathesis of cyclopropenone ketal: a one step synthesis of protected divinyl ketones

Cited by 32 publications

References 19 publications

Progress in Metathesis Through Natural Product Synthesis

Progress in Metathesis Through Natural Product Synthesis

Cross‐Metathesis in Natural Products Synthesis

The Joy and Challenge of Small Rings Metathesis

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