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Search for "Viburnum" in Full Text gives 2 result(s) in Beilstein Journal of Organic Chemistry.

Recent applications of the divinylcyclopropane–cycloheptadiene rearrangement in organic synthesis

Sebastian Krüger and
Tanja Gaich

Beilstein J. Org. Chem. 2014, 10, 163–193, doi:10.3762/bjoc.10.14

diterpene 5-epi-vibsanin E (115), from the plant Viburnum awabuki (see Scheme 14) [104]. Starting from triene 108 cyclopropanation was achieved using vinyldiazo compound 101. The fomal [4 + 3]-cycloaddition proceeded through cis-divinylcyclopropane 109 to yield rearranged cycloheptadiene 110. Desilylation

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Graphical Abstract

Scheme 1: Vogel’s first approach towards the divinylcyclopropane rearrangement [4] and characterization of cis-d...

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Scheme 2: Transition states for the Cope rearrangement and the related DVCPR. Ts = transition state.

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Scheme 3: Two possible mechanisms of trans-cis isomerizations of divinylcyclopropanes.

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Scheme 4: Proposed biosynthesic pathway to ectocarpene (21), an inactive degradation product of a sexual pher...

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Scheme 5: Proposed biosynthesis of occidenol (25) and related natural compounds.

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Scheme 6: Gaich’s bioinspired system using the DVCPR to mimick the dimethylallyltryptophan synthase. DMAPP = ...

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Scheme 7: Iguchi’s total synthesis of clavubicyclone, part 1.

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Scheme 8: Iguchi’s total synthesis of clavubicyclone, part 2.

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Scheme 9: Wender’s syntheses of the two pseudoguainanes confertin (50) and damsinic acid (51) and Pier’s appr...

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Scheme 10: Overman’s total synthesis of scopadulcic acid B.

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Scheme 11: Davies’ total syntheses of tremulenolide A and tremulenediol A.

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Scheme 12: Davies formal [4 + 3] cycloaddition approach towards the formal synthesis of frondosin B.

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Scheme 13: Davies and Sarpongs formal [4 + 3]-cycloaddition approach towards barekoxide (106) and barekol (107...

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Scheme 14: Davies formal [4 + 3]-cycloaddition approach to 5-epi-vibsanin E (115) containing an intermediate c...

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Scheme 15: Echavarren’s total synthesis of schisanwilsonene A (126) featuring an impressive gold-catalzed casc...

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Scheme 16: Davies early example of a formal [4 + 3]-cycloaddition in alkaloids synthesis.

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Scheme 17: Fukuyama’s total synthesis of gelsemine, part 1.

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Scheme 18: Fukuyama’s total synthesis of gelsemine, featuring a divinylcyclopropane rearrangement, part 2.

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Scheme 19: Kende’s total synthesis of isostemofoline, using a formal [4 + 3]-cycloaddition, including an inter...

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Scheme 20: Danishefsky’s total synthesis of gelsemine, part 1.

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Scheme 21: Danishefsky’s total synthesis of gelsemine, part 2.

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Scheme 22: Fukuyama’s total synthesis of gelsemoxonine.

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Scheme 23: Wender’s synthetic access to the core skeleton of tiglianes, daphnanes and ingenanes.

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Scheme 24: Davies’ approach towards the core skeleton of CP-263,114 (212).

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Scheme 25: Wood’s approach towards actinophyllic acid.

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Scheme 26: Takeda’s approach towards the skeleton of the cyanthins, utilitizing the divinylcyclopropane rearra...

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Scheme 27: Donaldson’s organoiron route towards the guianolide skeleton.

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Scheme 28: Stoltz’s tandem Wolff/DVCPR rearrangement.

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Scheme 29: Stephenson’s tandem photocatalysis/arylvinylcyclopropane rearrangement.

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Scheme 30: Padwa’s rhodium cascade involving a DVCPR.

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Scheme 31: Matsubara’s version of a DVCPR.

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Scheme 32: Toste’s tandem gold-catalyzed Claisen-rearrangement/DVCPR.

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Scheme 33: Ruthenium- and gold-catalyzed versions of tandem reactions involving a DVCPR.

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Scheme 34: Tungsten, platinum and gold catalysed cycloisomerizations leading to a DVCPR.

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Scheme 35: Reisman’s total synthesis of salvileucalin B, featuring an (undesired) vinylcyclopropyl carbaldehyd...

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Scheme 36: Studies on the divinylepoxide rearrangement.

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Scheme 37: Studies on the vinylcyclopropanecarbonyl rearrangement.

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Scheme 38: Nitrogen-substituted variants of the divinylcyclopropane rearrangement.

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Review

Published 16 Jan 2014

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End game strategies towards the total synthesis of vibsanin E, 3-hydroxyvibsanin E, furanovibsanin A, and 3-O-methylfuranovibsanin A

Brett D. Schwartz,
Craig M. Williams and
Paul V. Bernhardt

Beilstein J. Org. Chem. 2008, 4, No. 34, doi:10.3762/bjoc.4.34

-hydroxyvibsanin E; 3-O-methylfuranovibsanin A; natural products; terpenoids; vibsane; vibsanin E; Viburnum; Introduction Vibsane-type diterpenes occur exclusively in Viburnum species such as V. awabuki [1], V. odoratissimum [2] and V. suspensum [3], and can be regarded as quite rare natural products. Nine

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