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

• divinylcyclopropane–cycloheptadiene rearrangement starting in 1991. Earlier classic syntheses of sesquiterpenes are described to underline the synthetic power in the total synthesis of sesquiterpenoid natural products. The title reaction has been subject to previous reviews [5][6], partial overlap with the content of

• the cytotoxic sesquiterpenoid quadrone (55) from Aspergillus terreus [52][53] started from tricyclic ketone 52 [54], which was converted into tricycle 53 in 12 steps. Trans-divinylcyclopropane 53 underwent the desired DVCPR after trans-cis-isomerization of the vinyl moiety at 175 °C, forming bridged

• sesquiterpenoid sinularene (59) from the coral Sinularia mayi [58] started from alcohol 56, which was converted to bicyclic 57 in nine steps. Trans-divinylcyclopropane 57 was then subjected to high temperature DVCPR conditions furnishing bridged bicycle 58. Trans-cis isomerization of the vinyl moiety had to take

The chemistry of isoindole natural products

• Klaus Speck and
• Thomas Magauer

Beilstein J. Org. Chem. 2013, 9, 2048–2078, doi:10.3762/bjoc.9.243

• are unknown. The sesquiterpenoid stachyflin (156) was first isolated from the fungus Stachybotrys sp. RF-7260 by Shionogi & Co., Ltd., Japan, in 1997 [130] and shows outstanding antiviral activity against the influenza A subtype H1N1 (IC50 = 3 nM), outperforming current drugs such as amantadine and

Carbamate derivatives and sesquiterpenoids from the South China Sea gorgonian Melitodes squamata

• Li-Si Huang,
• Fei He,
• Hui Huang,
• Xiao-Yong Zhang and
• Shu-Hua Qi

Beilstein J. Org. Chem. 2012, 8, 170–176, doi:10.3762/bjoc.8.18

• rarely found in marine natural compounds, and 7 showed moderate antibacterial activity. The possible biosynthesis routes of 1–5 were conjectured. Keywords: carbamate; gorgonian; Melitodes squamata; sesquiterpenoid; Introduction Gorgonians are recognized to mainly produce acetogenins, sesquiterpenoids

• sesquiterpenoid with a methoxy group and a side chain that contained three methylene carbons. This suggestion was proved by the HMBC correlations (Figure 4). In the HMBC spectrum of 6, correlation of MeO– (δH 3.16, s) with δC 79.1 indicates the methoxygenation of C-10. The HMBC correlations of H-16 [δH 2.72 (d, J

Toward an integrated route to the vernonia allenes and related sesquiterpenoids

• Da Xu,
• Michael A. Drahl and
• Lawrence J. Williams

Beilstein J. Org. Chem. 2011, 7, 937–943, doi:10.3762/bjoc.7.104

• such structures are largely unexplored, we focused on the vernonia allenes. Moreover, we expected that such allenes contain the coded reactivity to access many sesquiterpenoid variants, especially in light of new methods of transforming allenes to diverse motifs [29][30][31][32][33][34][35][36][37