Total synthesis of decytospolides A, B and a formal synthesis of aspergillide A starting from d-mannitol via tandem/domino reactions by Grubb’s catalysts

Kammari, Bal Raju; Bejjanki, Naveen Kumar; Nagaiah, K.

doi:10.1016/j.tetasy.2015.01.014

Cited by 22 publications

(8 citation statements)

References 59 publications

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“…Another such application is the synthesis of the tetrahydropyran-containing natural products decytospolide A (336) and B (337) by Kommu and co-workers (Scheme 39), 173 which was rapidly achieved when the hydroxy olefin 338 was subjected to treatment by the H-G II catalyst (6) in the presence of pent-1-en-3-one to provide the pyrans 339 and 340 in 78% combined yield and as a 9:1 mixture of stereoisomers, in favor of the desired 2,6-cis-pyran 340. Re-…”

Section: Scheme 38 Total Synthesis Of Cyanolide Amentioning

confidence: 99%

Recent Advances in Total Synthesis via Metathesis Reactions

Cheng-Sánchez

Sarabia

2018

Synthesis

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The metathesis reactions, in their various versions, have become a powerful and extremely valuable tool for the formation of carbon–carbon bonds in organic synthesis. The plethora of available catalysts to perform these reactions, combined with the various transformations that can be accomplished, have positioned the metathesis processes as one of the most important reactions of this century. In this review, we highlight the most relevant synthetic contributions published between 2012 and early 2018 in the field of total synthesis, reflecting the state of the art of this chemistry and demonstrating the significant synthetic potential of these methodologies.1 Introduction2 Alkene Metathesis in Total Synthesis2.1 Total Synthesis Based on a Ring-Closing-Metathesis Reaction2.2 Total Synthesis Based on a Cross-Metathesis Reaction2.3 Strategies for Selective and Efficient Metathesis Reactions of Alkenes2.3.1 Temporary Tethered Ring-Closing Metathesis2.3.2 Relay Ring-Closing Metathesis2.3.3 Stereoselective Alkene Metathesis2.3.4 Alkene Metathesis in Tandem Reactions3 Enyne Metathesis in Total Synthesis3.1 Total Syntheses Based on a Ring-Closing Enyne-Metathesis Reaction3.2 Total Syntheses Based on an Enyne Cross-Metathesis Reaction3.3 Enyne Metathesis in Tandem Reactions4 Alkyne Metathesis in Total Synthesis4.1 Total Synthesis Based on a Ring-Closing Alkyne-Metathesis Reaction4.2 Other Types of Alkyne-Metathesis Reactions5 Conclusions

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Section: Scheme 38 Total Synthesis Of Cyanolide Amentioning

confidence: 99%

Recent Advances in Total Synthesis via Metathesis Reactions

Cheng-Sánchez

Sarabia

2018

Synthesis

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“…Tandem CM followed by intramolecular hetero‐Michael addition is a very attractive approach and this sequence was applied in a number of syntheses. Kommu and co‐workers reported the total synthesis of decytospolides A and B by tandem CM/Michael addition and aspergillide A by tandem CM/allyl S N 2′ substitution, in both cases using d ‐mannitol as a starting substrate (Scheme ) …”

Section: Defining Tandem Catalysismentioning

confidence: 99%

Tandem Catalysis Utilizing Olefin Metathesis Reactions

Zieliński

Grela

2016

Chemistry A European J

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Since olefin metathesis transformation has become a favored synthetic tool in organic synthesis, more and more distinct non-metathetical reactions of alkylidene ruthenium complexes have been developed. Depending on the conditions applied, the same olefin metathesis catalysts can efficiently promote isomerization reactions, hydrogenation of C=C double bonds, oxidation reactions, and many others. Importantly, these transformations can be carried out in tandem with olefin metathesis reactions. Through addition of one portion of a catalyst, a tandem process provides structurally advanced products from relatively simple substrates without the need for isolation of the intermediates. These aspects not only make tandem catalysis very attractive from a practical point of view, but also open new avenues in (retro)synthetic planning. However, in the literature, the term "tandem process" is sometimes used improperly to describe other types of multi-reaction sequences. In this Concept, a number of examples of tandem catalysis involving olefin metathesis are discussed with an emphasis on their synthetic value.

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“…The Fujioka group 6 reported that a novel, chemoselective in situ protection of enones as phosphonium silyl enol ethers using Ph 3 P and TMSOTf could be applied successively for the concise asymmetric total synthesis of decytospolides A and B. More recently, four other syntheses have been reported based on an intramolecular oxa-conjugate addition reaction by the Kommu 7 and Das 8 groups. Gómez and Fall groups reported using a [3,3]-sigmatropic rearrangement for the synthesis of 2,6-cis-tetrahydropyrans imbedded in 1 and 2.…”

Section: Figure 1 Decytospolides a And Bmentioning

confidence: 99%