Cyclobutyl Cation Rearrangements of 6-Protoilluden-8α-ol, 7-Protoilluden-6-ol and Related Compounds

NAOKO MORISAKI; JUN FURUKAWA; HISAYOSHI KOBAYASHI; SHIGEO IWASAKI; SHIGEO NOZOE; SHIGENOBU.OKUDA

doi:10.1248/cpb.35.2678

NAOKO MORISAKI, JUN FURUKAWA, HISAYOSHI KOBAYASHI, SHIGEO IWASAKI, SHIGEO NOZOE, SHIGENOBU.OKUDA

Author information

Keywords: sesquiterpene, 6-protoilluden-8α-ol, 7-protoilluden-6-ol, biomimetic reaction, formolysis, cyclobutyl cation rearrangement, Basidiomycete, 7-protoilludene C-6 cation

JOURNAL FREE ACCESS

1987 Volume 35 Issue 7 Pages 2678-2685

DOI https://doi.org/10.1248/cpb.35.2678

Details

Abstract

6-Protoilluden-8α-ol (15) was formolyzed and then reduced with LiAlH₄ to give 7-protoilluden-6-ol (16) and its stereoisomer (17). 3-epi-6-Protoilluden-8a-ol (19) also gave the same products under the same conditions. These and other related reactions imply that the 7-protoilludene C-6 cation (10) is an important intermediate in the biosynthesis of illudane (11), marasmane (12) and illudalane (13) type sesquiterpenes.

Corresponding author

Register with J-STAGE for free!