Premium
Partial Synthesis of Nitrogenous Brassinosteroid Analogues with 22,26‐Epiminocholestane and Spirosolane Skeleton
Author(s) -
Quyen Le Thi,
Adam Günter,
Schreiber Klaus
Publication year - 1994
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199419941115
Subject(s) - solasodine , brassinosteroid , chemistry , stereochemistry , lactone , steroid , alkaloid , sapogenin , solanum , botany , biochemistry , arabidopsis , gene , mutant , hormone , biology , medicine , alternative medicine , pathology
Starting with the known (22 S ,25 R )‐16β‐acetoxy‐ N ‐acetyl‐22,26‐epiminocholest‐5‐en‐3β‐ol ( 4 ), which has been prepared from the Solanum steroid alkaloid solasodine ( 3 ), we synthesized the nitrogenous brassinosteroid analogues (22 S ,25 R )‐2α,3α,16β‐trihydroxy‐22,26‐epimino‐5α‐cholestan‐6‐one ( 11 ), (25 R )‐2α,22α‐dihydroxy‐5α,22α N ‐spirosolan‐6‐one ( 13 ), (22 S ,25 R )‐2α,3α,16β‐trihydroxy‐22,26‐epimino‐6,7‐seco‐5α‐cholestano‐6,7‐lactone ( 15 ), and (25 R )‐2α‐3α‐dihydroxy‐6,7‐seco‐5α,22α N ‐spirosolano‐6,7‐lactone ( 18 ) as well as some of their derivatives.