TY - JOUR
T1 - Base‐Catalyzed Conversion of an Equatorial into an Axial Methoxycarbonyl Group Due to a 1,5‐Long‐Range Substituent Effect
AU - Mechoulam, Raphael
AU - Lander, Naftali
AU - Tamir, Ilana
AU - Ben‐Zvi, Zvi
AU - Kimmel, Yosef
PY - 1980/7
Y1 - 1980/7
N2 - The unusual transformation of an equatorial CO2Me group into an axial one has been observed in the hexahydrocannabinol skeleton [2a → 1a, R = Ac]. In the methyl ethers, however, the expected reaction takes place [1b → 2b, R = Me]. The epimerization of 2a in the presence of strong bases is attributed to the potential phenolate ion situated five carbon atoms away. (Figure Presented.)
AB - The unusual transformation of an equatorial CO2Me group into an axial one has been observed in the hexahydrocannabinol skeleton [2a → 1a, R = Ac]. In the methyl ethers, however, the expected reaction takes place [1b → 2b, R = Me]. The epimerization of 2a in the presence of strong bases is attributed to the potential phenolate ion situated five carbon atoms away. (Figure Presented.)
UR - http://www.scopus.com/inward/record.url?scp=84985569580&partnerID=8YFLogxK
U2 - 10.1002/anie.198005431
DO - 10.1002/anie.198005431
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AN - SCOPUS:84985569580
SN - 0570-0833
VL - 19
SP - 543
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 7
ER -