
TY  - JOUR
A1  - Brown, RFC 
A1  - Fallon, GD 
A1  - Gatehouse, BM 
A1  - Jones, CM 
A1  - Rae, ID 
T1  - Synthesis of the cyclopropa[c]benzofuran system of mycorrhizin A and of gilmicolin from a benzofuranol. Crystal structure of a 5,8-Methanocyclopropa-[c]naphtho[2,3-b]furan derivative
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1982
VL  - 35
IS  - 8
SP  - 1665
EP  - 1678
KW  - 
UR  - https://doi.org/10.1071/CH9821665 
N2  - The cyclopropa[c]benzofuran derivative (17), which contains the structural features of methyl ethers of mycorrhizin A and gilmicolin save for the C3 side chain, has been synthesized from the benzofuranol (4) through the benzofuran-4,7-dione (5) and the 7a-methoxy derivative (8). The cyclopropane ring of (17) was introduced by ultraviolet irradiation of a 1-pyrazoline (13) at -78º; irradiation at room temperature gave mainly a profoundly rearranged acidic product for which the methanoindenone structure (18) is proposed. The stereochemistry of the penultimate cyclopropane (16) has been established by X-ray crystallography. 
ER  -

