41943-79-7Relevant articles and documents
Bioconversion of Stemodia maritima diterpenes and derivatives by Cunninghamella echinulata var. elegans and Phanerochaete chrysosporium
Lamm, Andrew S.,Reynolds, William F.,Reese, Paul B.
, p. 1088 - 1093 (2008/02/10)
Stemodane and stemarane diterpenes isolated from the plant Stemodia maritima and their dimethylcarbamate derivatives were fed to growing cultures of the fungi Cunninghamella echinulata var. elegans ATCC 8688a and Phanerochaete chrysosporium ATCC 24725. C. echinulata transformed stemodin (1) to its 7α-hydroxy- (2), 7β-hydroxy- (3) and 3β-hydroxy- (4) analogues. 2α-(N,N-Dimethylcarbamoxy)-13-hydroxystemodane (6) gave 2α-(N,N-dimethylcarbamoxy)-6α,13-dihydroxystemodane (7) and 2α-(N,N-dimethylcarbamoxy)-7α,13-dihydroxystemodane (8). Stemodinone (9) yielded 14-hydroxy-(10) and 7β-hydroxy- (11) congeners along with 1, 2 and 3. Stemarin (13) was converted to the hitherto unreported 6α,13-dihydroxystemaran-19-oic acid (18). 19-(N,N-Dimethylcarbamoxy)-13-hydroxystemarane (14) yielded 13-hydroxystemaran-19-oic acid (17) along with the two metabolites: 19-(N,N-dimethylcarbamoxy)-2β,13-dihydroxystemarane (15) and 19-(N,N-dimethylcarbamoxy)-2β,8,13-trihydroxystemarane (16). P. chrysosporium converted 1 into 3, 4 and 2α,11β,13-trihydroxystemodane (5). The dimethylcarbamate (6) was not transformed by this microorganism. Stemodinone (9) was hydroxylated at C-19 to give 12. Both stemarin (13) and its dimethylcarbamate (14) were recovered unchanged after incubation with Phanerochaete.
Total Synthesis of (+/-)-Stemodin and (+/-)-Stemodinone
Corey, E.J.,Tius, Marcus A.,Das, Jagabandhu
, p. 7612 - 7613 (2007/10/02)
-