Chemical and Pharmaceutical Bulletin p. 1017 - 1023 (1995)
Update date:2022-08-04
Topics:
Tanaka
Okuda
Murakami
Yoshino
Mikamiyama
Kanda
Kim
Iwata
A novel and stereoselective spiroannelation reaction was developed. Treatment of the suitably functionalized cyclohexene derivative (3) with trimethylsilyl trifluoromethanesulfonate (TMSOTf) afforded the spiro[5.5]undecanes 4A and 5S exclusively. Changing the solvent from CH2Cl2 to CH3CN or THF increased the stereoselectivity, predominant formation of 4A in CH3CN and 5S in THF was observed. The spirocyclic compounds 4A and 5S were transformed into the tricyclo[6.3.1.01,6]dodecane derivatives (19A and 27S) corresponding to the B/C/D rings of aphidicolanes (1) and stemodanes (2).
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(1995)
