@article{b0a427ef0c5e434a9554db31aef4a3d8,
title = "A new type of cannabinoid. Synthesis of cannabielsoic acid A by a novel photo-oxidative cyclisation",
abstract = "Two tricyclic dihydrobenzofuran cannabinoids have been isolated and one of them has been synthesized by an intramolecular photo-oxidative cyclisation which involves attack by a phenoxy-group and molecular oxygen on a double bond.",
author = "A. Shani and R. Mechoulam",
note = "Funding Information: The stereochemistry at C-2-C-3 is probably cis. This is deduced from the fact that radical processes which form CHEMXCAL 1970COMMUNICATIONS, related tricyclic dihydrobenzofuran systems (cf. Pumerer{\textquoteright}s ketone4@) give the more stable cis-compounds. As a total synthesis of (V) has been reported* the con- version of (V) into (Ia) represents a formal total synthesis of the latter. The above reaction apparently represents the first recognized example of a new photo-oxidative cyclisation. A very recent publication{\textquoteright} describes a related oxidation, which, in our opinion, may be induced by light. We thank the U.S. National Institute of Mental Health for support of this work. (Received, January 5th, 1970; Corn. 022.) Y. Gaoni and R. Mechoulam, J. Amer. Chem. SOC.,1964,86, 1646. R. Mechoulam, P. Braun, and Y. Gaoni, J. Amer. Chem. SOC.,1967,89, 4662. a R. Mechoulam and Y. Gaoni, Tetrahedron, 1965,21, 1223. 4 D. H. R. Barton, A. M. Deflorin, and 0. E. Edwards, J. Chem. SOC.,1956, 530. 5 V. Arkley, F. M. Dean, A. Robertson, and P. Sidisunthorn, J. Chem. SOG.,* R. Mechoulam and 2.Ben-Zvi, Chem. Comm., 1969,343. 1956, 2322. ? D. M. Cahill and P. V. R. Shannon, J. Chem. SOG.(C),1969, 938.",
year = "1970",
month = jan,
day = "1",
doi = "10.1039/C29700000273",
language = "English",
pages = "273--274",
journal = "Journal of the Chemical Society D: Chemical Communications",
issn = "0577-6171",
publisher = "Royal Society of Chemistry",
number = "5",
}