185:
24:
404:
309:
639:
Harada, Kenichi; Makino, Kosho; Shima, Naoki; Okuyama, Haruka; Esumi, Tomoyuki; Kubo, Miwa; Hioki, Hideaki; Asakawa, Yoshinori; Fukuyama, Yoshiyasu (2013). "Total synthesis of riccardin C and (±)-cavicularin via Pd-catalyzed Ar–Ar cross couplings".
533:
Kostiuk, S. L.; Woodcock, T.; Dudin, L. F.; Howes, P. D.; Harrowven, D. C. (2011). "Unified
Syntheses of Cavicularin and Riccardin C: Addressing the Synthesis of an Arene Adopting a Boat Configuration".
471:
M. Toyota; T. Yoshida; Y. Kan; S. Takaoka; Y. Asakawa (1996). "(+)-Cavicularin: A Novel
Optically Active Cyclic Bibenzyl-Dihydrophenanthrene Derivative from the Liverwort Cavicularia densa Steph".
498:
David C. Harrowven; Timothy
Woodcock; Peter D. Howes (2005). "Total Synthesis of Cavicularin and Riccardin C: Addressing the Synthesis of an Arene That Adopts a Boat Configuration".
322:
569:
Takiguchi, H.; Ohmori, K.; Suzuki, K. (2013). "Synthesis and
Determination of the Absolute Configuration of Cavicularin by a Symmetrization/Asymmetrization Approach".
604:
Zhao, Peng; Beaudry, Christopher M. (2013). "Total
Synthesis of (±)-Cavicularin: Control of Pyrone Diels–Alder Regiochemistry Using Isomeric Vinyl Sulfones".
1306:
234:
684:
1049:
86:
868:
208:
InChI=1S/C28H22O4/c29-20-8-11-22-18(13-20)4-1-16-2-9-21(10-3-16)32-28-25(30)12-7-17-5-6-19-14-26(31)24(22)15-23(19)27(17)28/h2-3,7-15,29-31H,1,4-6H2
218:
InChI=1/C28H22O4/c29-20-8-11-22-18(13-20)4-1-16-2-9-21(10-3-16)32-28-25(30)12-7-17-5-6-19-14-26(31)24(22)15-23(19)27(17)28/h2-3,7-15,29-31H,1,4-6H2
1130:
1034:
1019:
1140:
1125:
1029:
1120:
1135:
989:
1115:
199:
1009:
1004:
999:
677:
1014:
994:
1024:
846:
1039:
778:
329:
1311:
1044:
861:
142:
1276:
163:
670:
1235:
1296:
1291:
1281:
389:
854:
1215:
896:
432:
36:
1075:
758:
754:
750:
1301:
1286:
952:
792:
348:
1230:
1195:
1179:
1175:
1171:
1167:
1163:
947:
180:
957:
911:
906:
901:
831:
774:
730:
725:
710:
52:
937:
814:
810:
797:
787:
783:
1225:
1220:
1100:
819:
802:
720:
381:
972:
1246:
1090:
1080:
702:
693:
621:
586:
551:
515:
377:
356:
1085:
106:
745:
649:
613:
578:
543:
507:
480:
369:
365:
257:
62:
151:
932:
662:
448:
436:
416:
412:
373:
352:
184:
877:
735:
716:
345:
300:
1270:
916:
484:
131:
40:
9,10,18,19-Tetrahydro-5,8:15,17-diethenobenzonaphthoxacyclotetradecin-3,12,21-triol
455:. In 2013, several other syntheses were reported for it and a racemic synthesis.
388:-substituted phenol ring is bent about 15° out of planarity, adopting a somewhat
823:
452:
393:
423:. The material was dried for one day, ground to a powder and 5 grams were
1110:
1070:
982:
977:
962:
942:
653:
397:
361:
285:
97:
364:
is unusual because it was the first compound isolated from nature displaying
881:
740:
625:
590:
582:
555:
547:
519:
511:
1105:
1095:
1065:
428:
403:
23:
420:
118:
617:
424:
299:
Except where otherwise noted, data are given for materials in their
967:
402:
85:
75:
431:
for 4 months to yield 2.5 mg (0.049%) of cavicularin after
850:
666:
168:
396:
in aromatic compounds is normally reserved for synthetic
447:
In 2005 and again in 2011, the compound was prepared by
1131:
9,10-dihydro-2,7-dihydroxy-3,4,6-trimethoxyphenanthrene
1020:
3-hydroxy-2,4,-dimethoxy-7,8-methylenedioxyphenanthrene
317:
242:
c1cc2ccc1CCc3cc(ccc3-c4cc-5c(cc4O)CCc6c5c(c(cc6)O)O2)O
1141:
9,10-dihydro-2,5-dihydroxy-3,4-dimethoxyphenanthrene
1126:
9,10-dihydro-2,7-dihydroxy-3,4-dimethoxyphenanthrene
1244:
1208:
1188:
1156:
1149:
1058:
1030:
2-hydroxy-3,5,7-trimethoxy-9,10-dihydrophenanthrene
925:
889:
767:
701:
1121:4,6-dimethoxy-9,10-dihydrophenanthrene-2,3,7-triol
380:for (+)-cavicularin is +168.2°. It is also a very
130:
1136:9,10-Dihydro-2,5-dimethoxyphenanthrene-1,7-diol
990:2,3,4-trimethoxy-7,8-methylenedioxyphenanthrene
61:
1116:4-methoxy-9,10-dihydrophenanthrene-2,3,7-triol
862:
678:
407:Cavicularin, three-dimensional representation
8:
1153:
1050:7-Hydroxy-2,3,4,8-tetramethoxyphenanthrene
1010:2,7-dihydroxy-3,4,9-trimethoxyphenanthrene
1005:2,7-dihydroxy-3,4,6-trimethoxyphenanthrene
1000:2,5-dihydroxy-3,4,9-trimethoxyphenanthrene
869:
855:
847:
685:
671:
663:
183:
105:
15:
150:
1015:2,7-Dihydroxy-3,6-dimethoxyphenanthrene
995:2,5-dihydroxy-3,4-dimethoxyphenanthrene
463:
239:
204:
179:
1025:2-hydroxy-3,5,7-trimethoxyphenanthrene
451:together with the unstrained compound
1040:4,6-dimethoxyphenanthrene-2,3,7-triol
1035:3,4,8-Trimethoxyphenanthrene-2,5-diol
211:Key: MCFLLKAHGNIXPF-UHFFFAOYSA-N
7:
1059:9,10-dihydrophenanthrene derivatives
884:(molecules with a C6-C2-C6 backbone)
1307:Heterocyclic compounds with 6 rings
221:Key: MCFLLKAHGNIXPF-UHFFFAOYAB
121:
1189:9,10-dihydrophenanthrene glycoside
1045:4,9-dimethoxyphenanthrene-2,5-diol
713:(3,3′-dihydroxy-5-methoxybibenzyl)
14:
779:13,13'-O-Isoproylidenericcardin D
307:
269:
22:
1249:-dihydrophenanthrene derivative
303:(at 25 °C , 100 kPa).
926:polyhydroxylated phenanthrenes
368:solely due to the presence of
275:
263:
1:
536:Chemistry: A European Journal
485:10.1016/0040-4039(96)00956-2
1328:
809:Macrocyclic bis(benzyls):
654:10.1016/j.tet.2013.06.064
297:
250:
230:
195:
45:
35:
30:
21:
1157:Phenanthrene glycosides
1236:8,8'-bidehydrojuncusol
583:10.1002/anie.201304929
548:10.1002/chem.201101550
512:10.1002/anie.200500466
408:
1209:dimeric phenanthrenes
433:column chromatography
406:
696:and their glycosides
571:Angew. Chem. Int. Ed
349:secondary metabolite
1312:Oxygen heterocycles
832:dihydrophenanthrene
731:Isonotholaenic acid
726:Dihydro-resveratrol
577:(40): 10472–10476.
542:(39): 10906–10915.
473:Tetrahedron Letters
419:in the district of
293: g·mol
18:
1277:Dihydrostilbenoids
1216:cirrhopetalanthrin
721:combretastatin B-1
703:Dihydrostilbenoids
694:Dihydrostilbenoids
415:was obtained from
409:
390:boat-like geometry
351:isolated from the
330:Infobox references
16:
1264:
1263:
1204:
1203:
1076:coeloginanthridin
844:
843:
648:(34): 6959–6968.
618:10.1021/ol303390a
506:(25): 3899–3901.
500:Angewandte Chemie
479:(27): 4745–4748.
378:specific rotation
357:Cavicularia densa
338:Chemical compound
336:
335:
164:CompTox Dashboard
87:Interactive image
1319:
1154:
871:
864:
857:
848:
830:Cyclic bibenzyl-
768:Oligomeric forms
751:Tyrolobibenzyl A
746:Notholaenic acid
687:
680:
673:
664:
658:
657:
636:
630:
629:
601:
595:
594:
566:
560:
559:
530:
524:
523:
495:
489:
488:
468:
392:. This type of
370:planar chirality
366:optical activity
346:natural phenolic
320:
314:
311:
310:
292:
277:
271:
265:
258:Chemical formula
188:
187:
172:
170:
154:
134:
123:
109:
89:
65:
26:
19:
1327:
1326:
1322:
1321:
1320:
1318:
1317:
1316:
1297:Total synthesis
1292:Diphenyl ethers
1282:Phenanthrenoids
1267:
1266:
1265:
1260:
1240:
1200:
1184:
1145:
1054:
953:dehydrojuncusol
933:coeloginanthrin
921:
885:
878:Phenanthrenoids
875:
845:
840:
793:Neomarchantin A
763:
697:
691:
661:
638:
637:
633:
606:Organic Letters
603:
602:
598:
568:
567:
563:
532:
531:
527:
497:
496:
492:
470:
469:
465:
461:
449:total synthesis
445:
443:Total synthesis
437:preparative TLC
417:Mount Ishizuchi
374:axial chirality
339:
332:
327:
326:
325: ?)
316:
312:
308:
304:
290:
280:
274:
268:
260:
246:
243:
238:
237:
226:
223:
222:
219:
213:
212:
209:
203:
202:
191:
173:
166:
157:
137:
124:
112:
92:
79:
68:
55:
41:
12:
11:
5:
1325:
1323:
1315:
1314:
1309:
1304:
1299:
1294:
1289:
1284:
1279:
1269:
1268:
1262:
1261:
1259:
1258:
1252:
1250:
1242:
1241:
1239:
1238:
1233:
1231:isoreptanthrin
1228:
1223:
1218:
1212:
1210:
1206:
1205:
1202:
1201:
1199:
1198:
1196:denneanoside F
1192:
1190:
1186:
1185:
1183:
1182:
1164:denneanoside A
1160:
1158:
1151:
1147:
1146:
1144:
1143:
1138:
1133:
1128:
1123:
1118:
1113:
1108:
1103:
1098:
1093:
1088:
1083:
1078:
1073:
1068:
1062:
1060:
1056:
1055:
1053:
1052:
1047:
1042:
1037:
1032:
1027:
1022:
1017:
1012:
1007:
1002:
997:
992:
986:
985:
980:
975:
970:
965:
960:
955:
950:
948:dehydroeffusol
945:
940:
935:
929:
927:
923:
922:
920:
919:
914:
909:
904:
899:
893:
891:
887:
886:
876:
874:
873:
866:
859:
851:
842:
841:
839:
838:
827:
826:
817:
806:
805:
800:
795:
790:
781:
775:Bis(bibenzyls)
771:
769:
765:
764:
762:
761:
748:
743:
738:
736:Lunularic acid
733:
728:
723:
717:Combretastatin
714:
707:
705:
699:
698:
692:
690:
689:
682:
675:
667:
660:
659:
631:
612:(2): 402–405.
596:
561:
525:
490:
462:
460:
457:
444:
441:
384:molecule. The
337:
334:
333:
328:
306:
305:
301:standard state
298:
295:
294:
288:
282:
281:
278:
272:
266:
261:
256:
253:
252:
248:
247:
245:
244:
241:
233:
232:
231:
228:
227:
225:
224:
220:
217:
216:
214:
210:
207:
206:
198:
197:
196:
193:
192:
190:
189:
181:DTXSID70745431
176:
174:
162:
159:
158:
156:
155:
147:
145:
139:
138:
136:
135:
127:
125:
117:
114:
113:
111:
110:
102:
100:
94:
93:
91:
90:
82:
80:
73:
70:
69:
67:
66:
58:
56:
51:
48:
47:
43:
42:
39:
33:
32:
28:
27:
13:
10:
9:
6:
4:
3:
2:
1324:
1313:
1310:
1308:
1305:
1303:
1300:
1298:
1295:
1293:
1290:
1288:
1285:
1283:
1280:
1278:
1275:
1274:
1272:
1257:
1254:
1253:
1251:
1248:
1243:
1237:
1234:
1232:
1229:
1227:
1224:
1222:
1219:
1217:
1214:
1213:
1211:
1207:
1197:
1194:
1193:
1191:
1187:
1181:
1177:
1173:
1169:
1165:
1162:
1161:
1159:
1155:
1152:
1148:
1142:
1139:
1137:
1134:
1132:
1129:
1127:
1124:
1122:
1119:
1117:
1114:
1112:
1109:
1107:
1104:
1102:
1099:
1097:
1094:
1092:
1089:
1087:
1084:
1082:
1079:
1077:
1074:
1072:
1069:
1067:
1064:
1063:
1061:
1057:
1051:
1048:
1046:
1043:
1041:
1038:
1036:
1033:
1031:
1028:
1026:
1023:
1021:
1018:
1016:
1013:
1011:
1008:
1006:
1003:
1001:
998:
996:
993:
991:
988:
987:
984:
981:
979:
976:
974:
971:
969:
966:
964:
961:
959:
958:flavanthrinin
956:
954:
951:
949:
946:
944:
941:
939:
936:
934:
931:
930:
928:
924:
918:
917:9-Phenanthrol
915:
913:
912:4-Phenanthrol
910:
908:
907:3-Phenanthrol
905:
903:
902:2-Phenanthrol
900:
898:
897:1-Phenanthrol
895:
894:
892:
888:
883:
879:
872:
867:
865:
860:
858:
853:
852:
849:
837:
833:
829:
828:
825:
821:
818:
816:
812:
808:
807:
804:
801:
799:
796:
794:
791:
789:
785:
782:
780:
776:
773:
772:
770:
766:
760:
756:
752:
749:
747:
744:
742:
739:
737:
734:
732:
729:
727:
724:
722:
718:
715:
712:
711:Batatasin-III
709:
708:
706:
704:
700:
695:
688:
683:
681:
676:
674:
669:
668:
665:
655:
651:
647:
643:
635:
632:
627:
623:
619:
615:
611:
607:
600:
597:
592:
588:
584:
580:
576:
572:
565:
562:
557:
553:
549:
545:
541:
537:
529:
526:
521:
517:
513:
509:
505:
501:
494:
491:
486:
482:
478:
474:
467:
464:
458:
456:
454:
450:
442:
440:
438:
434:
430:
426:
422:
418:
414:
405:
401:
399:
395:
391:
387:
383:
379:
375:
371:
367:
363:
359:
358:
354:
350:
347:
343:
331:
324:
319:
302:
296:
289:
287:
284:
283:
262:
259:
255:
254:
249:
240:
236:
229:
215:
205:
201:
194:
186:
182:
178:
177:
175:
165:
161:
160:
153:
149:
148:
146:
144:
141:
140:
133:
129:
128:
126:
120:
116:
115:
108:
104:
103:
101:
99:
96:
95:
88:
84:
83:
81:
77:
72:
71:
64:
60:
59:
57:
54:
50:
49:
44:
38:
34:
29:
25:
20:
1255:
938:confusaridin
890:Phenanthrols
835:
834:derivative:
811:Marchantin A
798:Plagiochin E
784:Marchantin B
645:
641:
634:
609:
605:
599:
574:
570:
564:
539:
535:
528:
503:
499:
493:
476:
472:
466:
446:
410:
394:angle strain
385:
355:
341:
340:
46:Identifiers
17:Cavicularin
1302:Cyclophanes
1287:Macrocycles
1256:Cavicularin
1226:reptanthrin
1221:flavanthrin
1101:loroglossol
836:Cavicularin
820:Riccardin B
803:Riccardin H
642:Tetrahedron
453:riccardin C
398:cyclophanes
342:Cavicularin
251:Properties
63:178734-41-3
1271:Categories
1150:glycosides
1111:Plicatol C
1071:coeloginin
983:Plicatol B
978:plicatol A
973:Perakensol
963:gymnopusin
943:confusarin
882:glycosides
880:and their
459:References
362:macrocycle
286:Molar mass
152:B6Y87G6TOX
98:ChemSpider
74:3D model (
53:CAS Number
37:IUPAC name
741:Lunularin
413:liverwort
353:liverwort
1247:bibenzyl
1106:orchinol
1096:juncusol
1091:hircinol
1081:coelonin
1066:coelogin
626:23301524
591:23956143
556:21932232
520:15900530
429:methanol
425:refluxed
382:strained
132:11316166
1245:Cyclic
1086:effusol
421:Shikoku
360:. This
323:what is
321: (
291:422.480
119:PubChem
107:9491133
624:
589:
554:
518:
376:. The
318:verify
315:
235:SMILES
31:Names
968:Nudol
344:is a
200:InChI
76:JSmol
1178:and
822:and
813:and
786:and
757:and
719:and
622:PMID
587:PMID
552:PMID
516:PMID
435:and
411:The
386:para
372:and
143:UNII
650:doi
614:doi
579:doi
544:doi
508:doi
481:doi
427:in
169:EPA
122:CID
1273::
1174:,
1170:,
1166:,
777::
753:,
646:69
644:.
620:.
610:15
608:.
585:.
575:52
573:.
550:.
540:17
538:.
514:.
504:44
502:.
477:37
475:.
439:.
400:.
273:22
267:28
1180:E
1176:D
1172:C
1168:B
870:e
863:t
856:v
824:C
815:C
788:E
759:C
755:B
686:e
679:t
672:v
656:.
652::
628:.
616::
593:.
581::
558:.
546::
522:.
510::
487:.
483::
313:N
279:4
276:O
270:H
264:C
171:)
167:(
78:)
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