cavicularin

the goodman group
university of cambridge

cavicularin

Notes This molecule is chiral. The absolute configuration is not known. The three-dimensional picture, above, may show the natural product or may be its enantiomer. The InChI (version 1) naming system cannot distinguish the two forms of this non-local stereochemistry.

Literature (+)-Cavicularin: A Novel Optically Active Cyclic Bibenzyl-Dihydrophenanthrene Derivative from the Liverwort Cavicularia densa Steph.
M. Toyota, T. Yoshida, Y. Kan, S. Takaoka and Y. Asakawa. Tetrahedron Letters 1996, 37, 4745-4748.
DOI: 10.1016/0040-4039(96)00956-2

Total Synthesis of Cavicularin and Riccardin C: Addressing the Synthesis of an Arene That Adopts a Boat Configuration
D. C. Harrowven, T. Woodcock and P. D. Howes. Angew. Chem. 2005, 44, 3899-3901.
DOI: 10.1002/anie.200500466

SMILES

OC1=C(O[C@@]2=CC=[C@]3C=C2)C(C4=C[C@]([C@@]5=C(C3)C=[C@](O)C=C5)=C(O)C=C4CC6)=[C@]6C=C1

Canonical SMILES

InChI
InChI=1/C27H20O4/c28-19-6-9-21-18(12-19)11-15-1-7-20(8-2-15)31-27-24(29)10-5-16-3-4-17-13-25(30)23(21)14-22(17)26(16)27/h1-2,5-10,12-14,28-30H,3-4,11H2
AuxInfo=1/0/N:25,27,21,20,10,18,24,28,19,11,29,16,3,6,26,9,4,15,17,23,8,5,1,12,2,7,13,31,22,30,14/E:(1,2)(7,8)/rA:31nCCCCCCCCCCCCCOCCCCCCCOCCCCCCCOO/rB:d1;s2;d3;s4;p1d5;s5;s1;d7;P9;d10;s11;s7d12;s13;d8;s15;d16;P17;p8d18;s4;P9s20;s12;s14;d23;s24;d25;P26;p23d27;s15s26;s2;s17;/rC:-.2739,-.6223,0;-.2739,-1.4473,0;.4406,-1.8598,0;1.1551,-1.4473,0;1.1551,-.6223,0;.4406,-.2098,0;1.952,-.4087,0;-1.0707,-.4087,0;2.5353,-.9921,0;3.3322,-.7786,0;3.5457,.0183,0;2.9624,.6017,0;2.1655,.3882,0;1.753,1.1026,0;-1.4832,.3057,0;-2.3082,.3057,0;-2.7207,-.4087,0;-2.3082,-1.1232,0;-1.4832,-1.1232,0;1.7384,-2.0306,0;2.5353,-1.8171,0;3.1759,1.3986,0;.9561,1.3162,0;.5436,2.0306,0;-.2814,2.0306,0;-.6939,1.3162,0;-.2814,.6017,0;.5436,.6017,0;-1.4832,1.1307,0;-.8572,-2.0306,0;-3.5457,-.4087,0;

MInChI v0.9
MInChIxe1 C27H20O4 c28xh19xh6xh 9xh21xh18xl1 2xh19xr11xh1 5xh1xh7xh20x l8xh2xh15xr3 1xh27xh24xl2 9xr10xh5xh16 xh3xh4xh17xh 13xh25xl30xr 23xl21xr14xh 22xl17xr26xl 16xr27xsh1xh 2xc5xh10xc12 xh14xc28xh30 Hxc3xh4xc11H 2

Structure files

MOL file ; PDB file

Conformation
1000 step GACK search using MMFF forcefield

Updated: 16 June 2006