6102-38-1Relevant articles and documents
Yang,Chen
, p. 530 (1971)
Regiodivergent Remote Arylation of Cycloalkanols to Dysideanone′s Fused Carbotetracycles and Its Bridged Isomers
Haque, Md Ashraful,Jana, Chandan K.
supporting information, p. 13300 - 1330 (2017/09/11)
Regiodivergent γ and γ′ arylations across an all-carbon quaternary center of cycloalkanols to access enantioenriched fused and bridged carbotetracycles are reported. The conformation of the carbocation guided either sequential stereospecific β-C-Me/γ-C?H-shifts or β-C-Me/γ′-C?H-shifts, providing fused carbotetracyclic analogs of dysideanone or bridged tetracycles, respectively. The reaction is highly stereoselective in building three contiguous stereocenters, where one, two, or three could be all-carbon quaternary centers. Interestingly, mechanistic studies revealed a crucial role of a methyl substituent in controlling regioselectivity.
Preparative Bioorganic Chemistry, XVII. Reduction of a Prochiral Diketone, 9-Methyl-trans-decalin-1,8-dione, with Baker's Yeast
Mori, Kenji,Takayama, Shuichi,Yoshimura, Seiji
, p. 91 - 96 (2007/10/02)
Reduction of 9-methyl-trans-decalin-1,8-dione (1) with baker's yeast affords (8S,9R,10R)-8-hydroxy-9-methyl-trans-1-decalone (8) as the major product in 47percent yield.Its (8S,9S,10S)-isomer (9, 14percent yield) and (1S,8S)-9-methyl-trans-1,8-diol (10, 7percent yield) are obtained as minor products.Baker's yeast cannot reduce 9-methyl-cis-decalin-1,8-dione (2). Key Words: Asymmetric reduction / Baker's yeast / Yeast / Saccharomyces cerevisia / Enzymes / trans-1-Decalone derivatives / trans-1,8-Decalindione derivatives