Synthesis of the Core Structure of Salicylihalamide A by Intramolecular Suzuki Reaction

Bauer, Matthias; Maier, Martin E.

doi:10.1021/ol026040k

Cited by 43 publications

(16 citation statements)

References 51 publications

(33 reference statements)

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“…224d Bauer and Maier synthesized the benzolactone 538, which has the core structure of salicylihalamide A, using intramolecular Suzuki reaction. 228 Hydroboration of the alkenyl iodide-alkene 537 with 9-BBN and subsequent Suzuki reaction in the presence of a palladium catalyst gave the macrolactone 538 in 48% yield (Scheme 160). The hydroboration proceeded with high diastereoselectivity.…”

Section: Scheme 156mentioning

confidence: 99%

Transition-Metal-Catalyzed Reactions in Heterocyclic Synthesis

2004

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Section: Scheme 156mentioning

confidence: 99%

Transition-Metal-Catalyzed Reactions in Heterocyclic Synthesis

2004

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“…This was accomplished in high yield by the method we had previously described. [33] Thus, tosylation of the alcohol 20 and subsequent heating of the tosylate 21 at reflux in glyme (1,2-dimethoxyethane) in the presence of NaI (2.5 equiv.) and DBU (5.0 equiv.)…”

Section: Introductionmentioning

confidence: 99%

Flexible Routes to the 5‐Hydroxy Acid Fragment of the Cryptophycins

2003

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Two solutions to establishing the anti stereochemistry of the vicinal stereocenters in the 5-hydroxy acid subunit of cryptophycin, based on initial Evans syn aldol reactions between an N-(propionyl)oxazolidinone 4 and a C 3 aldehyde, were developed. In the first route, the secondary hydroxy group was inverted by use of Mitsunobu reaction conditions, whereas the second route features an inversion of the methyl-bearing stereocenter, achieved by reductive removal

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“…Here a diastereoselective hydroboration generated the stereocenter at C12 prior to the coupling step. 36 This strategy was also successful in the reverse order. Thus, hydroboration of fragment 48 followed by coupling with vinyl iodide 47 gave rise to seco compound 49.…”

Section: Organic and Biomolecular Chemistry Reviewmentioning

confidence: 97%

Design and synthesis of analogues of natural products

Maier

2015

Org. Biomol. Chem.

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139

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In this article strategies for the design and synthesis of natural product analogues are summarized and illustrated with some selected examples. Proven strategies include diverted total synthesis (DTS), function-oriented synthesis (FOS), biology-oriented synthesis (BIOS), complexity to diversity (CtD), hybrid molecules, and biosynthesis inspired synthesis. The latter includes mutasynthesis, the synthesis of natural products encoded by silent genes, and propionate scanning. Most of the examples from our group fall in the quite general concept of DTS. Thus, in case an efficient strategy to a natural product is at hand, modifications are possible at almost any stage of a synthesis. However, even for compounds of moderate complexity, organic synthesis remains a bottle neck. Unless some method for predicting the biological activity of a designed molecule becomes available, the design and synthesis of natural product analogues will remain what it is now, namely it will largely rely on trial and error.

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Synthesis of the Core Structure of Salicylihalamide A by Intramolecular Suzuki Reaction

Abstract: [reaction: see text] An intramolecular Suzuki coupling was used to establish the core structure of the benzolactone enamide salicylihalamide A. This strategy combines a diastereoselective hydroboration with a subsequent cross-coupling.

Cited by 43 publications

References 51 publications

Transition-Metal-Catalyzed Reactions in Heterocyclic Synthesis

Transition-Metal-Catalyzed Reactions in Heterocyclic Synthesis

Flexible Routes to the 5‐Hydroxy Acid Fragment of the Cryptophycins

Design and synthesis of analogues of natural products

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