Preparation of 13- to 19-membered carbocycles (metacyclophanes) from 1,3-disubstituted benzene derivatives has been successfully carried out using the RCM reaction, but similar starting materials having diphenyl ether did not cyclize to 15-membered compounds, whose ground state conformations were calculated and discussed. Several attempts to cyclize to form platycarynol are described.
KaneVV. (1994) Synthesis of small cyclophanes. Tetrahedron, 50, 4575-4622.
2.
SchwabP, GrubbsRH, ZillerJW. (1996) Synthesis and applications of RuCl2(=CHR')(PR3)2: The influence of the alkylidene moiety on metathesis activity. Journal of the American Chemical Society, 118, 100-110.
3.
SchwabP, FranceMB, ZillerJW, GrubbsRH. (1995) A series of well-defined metathesis catalysts-synthesis of [RuCl2(CHR)(PR3)2] and its reactions. Angewandte Chemie International Edition English, 34, 2039-2041.
4.
SchollM, TrnkaTM, MorganJP, GrubbsRH. (1999) Increased ring closing metathesis activity of ruthenium-based olefin metathesis catalysts coordinated with imidazolin-2-ylidene ligands. Tetrahedron Letters, 40, 2247-2250.
5.
SchrockRR, MurdzekJ-S, BazanGC, RobbinsJ, DiMareM, O'ReganM. (1990) Synthesis of molybdenum imido alkylidene complexes and some reactions involving acyclic olefins. Journal of the American Chemical Society, 112, 3875-3886
ToriM, MizutaniR. (2010) Construction of eight-membered carbocycles with trisubstituted double bonds using the ring closing metathesis reaction. Molecules, 15, 4242-4260.
8.
FürstnerA, LangemannK. (1997) Macrocycles by ring-closing metathesis. Synthesis, 792-803.
9.
SabithaG, SwapnaR, BabuRS, YadavJS. (2005) Synthetic studies toward pondaplin: total synthesis of pondaplin analogues. Tetrahedron Letters, 46, 6145-6148.
10.
MorieY, SuzukiY, IkedaK, SatoM. (2005) Synthesis of 2-pyrones bridged at the 3- and 6-positions by ring-closing metathesis. Heterocycles, 65, 1167-1176.
11.
RamanaCV, MondalMA, PuranikVG, GurjarMK. (2006) Synthetic studies toward macrocidins: an RCM approach for the construction of the central cyclic core. Tetrahedron Letters, 47, 4061-4064.
12.
TaeJ, YangYK. (2003) Efficient synthesis of macrocyclic paracyclophanes by ring-closing metathesis dimerization and trimerization reactions. Organic Letters, 5, 741-744.
13.
LiuJX, SaitoS, YamamotoY. (2000) Preparation of functionalized metacyclophanes by intramolecular benzannulation of bisenynes. Tetrahedron Letters, 41, 4201-4204.
14.
WangH, WulffWD., (1998) Macrocyclization of Fischer carbene complexes as an approach to cyclophanes. Journal of the American Chemical Society, 120, 10573-10574
15.
WangH, WulffWD. (2000) Unexpected regiochemistry in the benzannulation reaction of Fischer carbene complexes in the synthesis of cyclophanes. Journal of the American Chemical Society, 122, 9862-9863.
16.
NakashimaK, ImotoM, MikiT, MiyakeT, FujisakiN, FukunagaS, MizutaniR, SonoM, ToriM. (2002) Ring closing metathesis reaction of dienes with acrylate moiety leading to 5- to 7-membered lactones and cyclization to 14-membered rings. Heterocycles, 56, 85-89.
17.
NagaiM, KudoM, InoueT, MatsuoM. (1976) Acerogenin A, a novel cyclic diarylheptanoid. Journal of the Chemical Society, Chemical Communications, 338-339.
18.
GonzalezGI, ZhuJ. (1999) A unified strategy toward the synthesis of acerogenin-type macrocycles: Total syntheses of acerogenins A, B, C, and L and aceroside IV. The Journal of Organic Chemistry, 64, 914-924.
19.
TanakaT, JiangZH, KounoI. (1998) Distribution of ellagic acid derivatives and a diarylheptanoid in wood of Platycarya strobilacea.Phytochemistry, 47, 851-854.
AkihisaT, TaguchiY, YasukawaK, TokudaH, AkazawaH, SuzukiT, KimuraY. (2006) Acerogenin M, a cyclic diarylheptanoid, and other phenolic compounds from Acer nikoense and their anti-inflammatory and anti-tumor-promoting effects. Chemical and Pharmaceutical Bulletin, 54, 735-739.
23.
AkazawaH, AkihisaT, TaguchiY, BannoN, YoneimaR, YasukawaK. (2006) Melanogenesis inhibitory and free radical scavenging activities of diarylheptanoids and other phenolic compounds from the bark of Acer nikoense.Biological and Pharmaceutical Bulletin, 29, 1970-0972
24.
InoueT. (1993) Constituents of Acer nikoense and Myrica rubra. On diarylheptanoid. Yakugaku Zasshi, 113, 181-197.
25.
GotoH, OsawaE. (1989) Corner flapping: A simple and fast algorithm for exhaustive generation of ring conformations. Journal of the American Chemical Society, 111, 8950-8951
26.
GotoH, OsawaE. (1993) An efficient algorithm for searching low-energy conformers of cyclic and acyclic molecules. Journal of the Chemical Society, Perkin Transactions2, 187-198.