Journal of Organic Chemistry p. 2300 - 2306 (1981)
Update date:2022-08-11
Topics:
Nakazaki, Masao
Naemura, Koichiro
Chikamatsu, Hiroaki
Iwasaki, Masami
Hashimoto, Masaki
A modification of Barborak's trishomocubane synthesis, when applied to the higher homologue, afforded 8,12-diacetoxy-C2-bismethanotwistane (21) which was converted into (+/-)-4-C2-methanoditwistanone (29) by a sequence of conversions involving diazomethane ring expansion of the intermediate keto acetates 24 and 25.Incubation of the resulting C2-ketone 29 with Rhodotorula rubra yielded a mixture of the (-)-C2-ketone 29 and the (+)-C2-alcohol 28 with respective 15percent and 33percent optical purities.Our proposed microbial C2-ketone rule coupled with CD analysis assigned the 3S,5S configuration to the (-)-C2-ketone 29 whose Wolff-Kishner reduction gave (-)-C2-methanoditwistane (9).Demjanov rearrangement of the amine 31 prepared from the (-)-C2-ketone 29 followed by removal of the functional group provided (-)-D3-tritwistane (10) (
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Doi:10.1039/c39810000257
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