Synthesis, Fragmentation, and Rearrangement Reactions of Annelated Cyclobutylcarbinols
04 August 2005 (online)
New tricyclic annelated cyclobutylcarbinols are synthesized diastereoselectively. Acid-induced fragmentation and Wagner-Meerwein rearrangement of these alcohols to give bicyclic dienes and annelated norbornanes are reported.
fused-ring systems - carbocations - rearrangements - ring opening - cycloadditions
BreitmaierE. Terpene Teubner Studienbücher Chemie; Leipzig: 1999.
Lee-RuffE. MladenovaG. Chem. Rev. 2003, 103: 1449
NamysloJC. KaufmannDE. Chem. Rev. 2003, 103: 1485
PirrungMC. J. Am. Chem. Soc. 1979, 101: 7130
PirrungMC. J. Am. Chem. Soc. 1981, 103: 82
CoreyEJ. J. Am. Chem. Soc. 1964, 86: 1652
RanuBC. SarkarDC. BasuMK. Tetrahedron 1989, 45: 3107
LangeGL. GottardoC. Magn. Reson. Chem. 1996, 34: 660
- 5c As already mentioned in ref. 5b the photocycloaddition of cyclopentene to 1 yields a mixture of diastereomers with 2a and its cis,syn,cis-isomer in a 9:1 ratio. For more details see:
GrotaJ. PhD Thesis University of Bielefeld; Germany: 2004. 44. p.158
SullivanBW. FaulknerDJ. J. Org. Chem. 1986, 51: 5134
ArmaregoWLF. PerrinDD. In Purification of Laboratory Chemicals 4th ed.: Butterworth-Heinemann; Oxford: 1996. p.Chapt. 2
The relative configuration of 2d was determined from 9b by NMR following the reaction sequence 2d Æ 3e Æ 9b.9
The supplementary crystallographic data for this structure (CCDC 237662) can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, by e-mailing email@example.com, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK.10
The supplementary crystallographic data for this structure (CCDC 237661) can be obtained free of charge as described in ref. 9.