Tricyclic challenges: synthetic approaches toward dodecahydrocyclopenta[a]indenes

Krebs, Michaël; Kalinowski, Matthäus; Frey, Wolfgang; Claasen, Birgit; Baro, Angelika; Schobert, Rainer

doi:10.1016/j.tet.2013.06.070

Cited by 2 publications

(2 citation statements)

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“…Aldol condensation in the presence of t-BuOK gave the tricyclic derivative 69. 58 Despite the poor yield of 18%, no evidence for a retro-aldol reaction was found.…”

Section: Account Synlettmentioning

confidence: 99%

“…To gain access to the tricyclic core units of the tetramic acid macrolactams discodermide (53), 53 isolated from the sponge Discodermia dissoluta, 54,55 and maltophilin (54), 56,57 we envisaged the use of the tricyclic hydroxyketone 55 as a synthetic precursor (Scheme 13). 58 We hoped that compound 55 might be obtained from an intramolecular aldol addition of hydropentalene 56, which could be traced back to the enone 44 and an organometallic reagent 57, the former being traced back to the C 2 -symmetrical diketone 43.…”

Section: Account Syn Lettmentioning

confidence: 99%

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Adventures and Detours in the Synthesis of Hydropentalenes

Deimling

Zens

Park

et al. 2020

Synlett

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Functionalized hydropentalenes (i.e., bicyclo[3.3.0]octanones) constitute important building blocks for natural products and for ligands for asymmetric catalysis. The assembly and tailored functionalization of this convex roof-shaped scaffold is challenging and has motivated a variety of synthetic approaches including our own contributions, which will be presented in this account.1 Introduction2 Biosynthesis of Hydropentalenes3 Hydropentalenes through the Pauson–Khand Reaction4 Hydropentalenes through Transannular Oxidative Cyclization of Cycloocta-1,4-diene5 Functionalization of Bicyclo[3.3.0]octan-1,4-dione to Dodecahydrocyclopenta[a]indenes6 Functionalization of Bicyclo[3.3.0]octan-1,4-diones to Crown Ether Hybrids7 Functionalization of Bicyclo[3.3.0]octan-1,4-dione to Cylindramide8 Tandem Ring-Opening Metathesis/Ring-Closing Metathesis/Cross-Metathesis of Bicyclo[2.2.1]heptanes9 Functionalization of Bicyclo[3.3.0]octan-1,4-dione to Geodin A10 Hydropentalenes through Enantioselective Desymmetrization of Weiss Diketones11 Functionalization of Weiss Diketones by Carbonyl Ene Reactions12 Functionalization of the Weiss Diketone to Cylindramide and Geodin A Core Units13 Biological Properties of Bicyclo[3.3.0]octanes14 Hydropentalenes through Vinylcyclopropane Cyclopentene Rearrangement15 Functionalization of Bicyclo[3.3.0]octanes toward Chiral Dienes16 Miscellaneous Syntheses of Hydropentalenes17 Conclusion and Outlook

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“…Aldol condensation in the presence of t-BuOK gave the tricyclic derivative 69. 58 Despite the poor yield of 18%, no evidence for a retro-aldol reaction was found.…”

Section: Account Synlettmentioning

confidence: 99%