59372-72-4Relevant academic research and scientific papers
Iterative three-carbon annelations. Synthesis of (±)-hirsutene
Greene, Andrew E.
, p. 3059 - 3060 (1980)
A short, flexible approach to the tricyclopentanoid carbon skeleton of the hirsutane group is illustrated by the synthesis of (±)-hirsutene (3).
Catalytic, asymmetric transannular aldolizations: Total synthesis of (+)-hirsutene
Chandler, Carley L.,List, Benjamin
, p. 6737 - 6739 (2008/12/22)
We report an asymmetric, catalytic transannular aldolization that provides polycyclic products useful for natural product synthesis. We found that a proline-derivative catalyzes the transannular aldol reaction of 1,4-cyclooctanediones to the corresponding cyclic β-hydroxy ketones in good yields and with high enantioselectivities. The utility of our reaction has been demonstrated in a total synthesis of (+)-hirustene. Copyright
Asymmetric Synthesis of (+)-Hirsutene
Hua, Duy H.,Venkataraman, S.,Ostrander, Robert A.,Sinai, Gurudas-Z.,McCann, Peggy J.,et al.
, p. 507 - 515 (2007/10/02)
The asymmetric total synthesis of (+)-hirsutene from the regio- and enantioselective 1,4-γ-addition reaction of (-)-(S)-allyl p-tolyl sulfoxide and 2-methyl-2-cyclopentenone is presented.In this total synthesis, a facile ring closure reaction involving enol thioether and enol acetate moieties and the deoxygenation reaction of a highly hindered secondary alcohol via its 2-propanesulfonate were found.An unexpected displacement reaction at the sulfur atom of alkenyl sulfoxides and the addition reactions of the cis sulfinylallyl anions with cyclic enones were also observed during the studies.
