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

• rearrangement was followed by MOM-cleavage. Oxidation furnished an intermediate aldehyde, followed by Wacker oxidation and the Anders–Gaßner variant [106][107][108][109] of the Wittig reaction to furnish 5-epi-vibsanin E (115). Echavarren and coworkers [110] used a DVCPR to target the sesquiterpenoid

• formal [4 + 3]-cycloaddition approach towards barekoxide (106) and barekol (107), involving a DVCPR. Davies formal [4 + 3]-cycloaddition approach to 5-epi-vibsanin E (115) containing an intermediate cis-divinylcyclopropane and the corresponding DVCPR. Echavarren’s total synthesis of schisanwilsonene A

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

• Brett D. Schwartz Craig M. Williams Paul V. Bernhardt School of Molecular and Microbial Sciences, University of Queensland, Brisbane, 4072, Queensland, Australia 10.3762/bjoc.4.34 Abstract End game synthetic strategy studies towards the total synthesis of the vibsanin type diterpenes, vibsanin E

• -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

• structure subtypes have so far been isolated from this family, for example, vibsanin B (1) [1], vibsanin C (2) [1], vibsanin E (3) [1], vibsanin O (4) [4], cyclovibsanin A (5) [5], furanovibsanin D (6) [6], spirovibsanin A (7) [7], aldolvibsanin B (8) [8], and neovibsanin A (9) [9] (Figure 1). In previous